홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Triethylamine → N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamide

HRID 662126
노트
인쇄 미리보기

반응식

HRID 662126 반응식
CC(C1CN(CC2C=C(C3C=C(CNC(C4C=CC=C(C(NC[C:38]5[C:39]([NH:51][CH:52]6[CH2:57][CH2:56][O:55][CH2:54][CH2:53]6)=[C:40]6[CH:48]=[N:47][N:46]([CH2:49][CH3:50])[C:41]6=[N:42][C:43]=5[CH2:44][CH3:45])=O)N=4)=O)C=CC=3C)C=CC=2)CCN1C([O-])=O)(C)C.C(N1[C:68]2=N[C:70]([CH2:93][CH3:94])=[C:71]([CH2:80][NH:81][C:82]([C:84]3[N:89]=[C:88]([C:90]([OH:92])=O)[CH:87]=[CH:86][CH:85]=3)=[O:83])[C:72](NC3CCOCC3)=[C:67]2C=N1)C.NCC1C=[C:99]([C:103]2C=C[CH:106]=[C:105]([CH2:109][CH:110]3[CH2:115][CH2:114][N:113]([C:116](OC(C)(C)C)=O)[CH2:112][CH2:111]3)[CH:104]=2)C=CC=1.[CH3:123][N:124](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[CH2:49]([N:46]1[C:41]2=[N:42][C:43]([CH2:44][CH3:45])=[C:38]([CH2:123][NH:124][C:90]([C:88]3[CH:87]=[CH:86][CH:85]=[C:84]([C:82]([NH:81][CH2:80][C:71]4[CH:70]=[C:93]([C:94]5[CH:99]=[CH:103][CH:104]=[C:105]([CH2:109][CH:110]6[CH2:115][CH2:114][N:113]([CH3:116])[CH2:112][CH2:111]6)[CH:106]=5)[CH:68]=[CH:67][CH:72]=4)=[O:83])[N:89]=3)=[O:92])[C:39]([NH:51][CH:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)=[C:40]2[CH:48]=[N:47]1)[CH3:50]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57813360tert-Butyl 4-{[3'-(aminomethyl)biphenyl-3-yl]methyl}piperidine-1-carboxylateHCID 578193746-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid
HCID 86633354
1,1-Dimethylethyl-4-[(5'-{[({6-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinyl}carbonyl)amino]methyl}-2'-methyl-3-biphenylyl)methyl]-1-piperazinecarboxylate

생성물 1

HCID 44193617N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamide수율 22.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Process (A) A mixture of 6-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid (84 mg, 0.186 mmol), 1,1-dimethylethyl 4-{[3′-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate (54.7 mg, 0.186 mmol), HBTU (o-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (84 mg, 0.223 mmol) and Et3N (0.129 mL, 0.928 mmol) in DCM (3 mL) was stirred at room temperature overnight. The crude mixture was quenched with saturated NaHCO3, and extracted with DCM twice. The combined organic layers were washed with brine and then concentrated under vacuum to give crude residue. The crude product was purified with a Gilson HPLC (with 0.1% TFA in the solvents), eluting with 10 to 70% CH3CN in water at a flow rate of 20 mL/min. The product fractions were combined, converted to the free base with saturated NaHCO3 and the basified solution was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-({3′-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamide as a white solid (30 mg, 22.2%). LC-MS m/z 729 (M+H)+, 0.80 min (ret time).

후처리

  1. customThe crude mixture was quenched with saturated NaHCO3
  2. extractionextracted with DCM twice
  3. washThe combined organic layers were washed with brine
  4. concentrationconcentrated under vacuum
  5. customto give crude residue
  6. customThe crude product was purified with a Gilson HPLC (with 0.1% TFA in the solvents),
  7. washeluting with 10 to 70% CH3CN in water at a flow rate of 20 mL/min
  8. extractionthe basified solution was extracted with ethyl acetate twice
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-a4dc6b71f51849aca2669394241d3e6f
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084449B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트