Sodium Bicarbonate → HCID 59507053, 화합물

HRID 1800732노트

반응식

HRID 1800732 반응식
[NH2:1][C:2]1[S:3][C:4]2[N:5]=[C:6]([NH:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:32])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[CH:22]=4)[CH:15]=[CH:16][C:17]=3[CH3:18])[N:7]=[CH:8][C:9]=2[N:10]=1.[CH3:33][CH:34]([C:36]1[NH:40][N:39]=[C:38]([C:41](O)=[O:42])[CH:37]=1)[CH3:35].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:30]([C:27]([C:23]1[CH:22]=[C:21]([C:20]([NH:19][C:14]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([NH:11][C:6]3[N:7]=[CH:8][C:9]4[N:10]=[C:2]([NH:1][C:41]([C:38]5[CH:37]=[C:36]([CH:34]([CH3:35])[CH3:33])[NH:40][N:39]=5)=[O:42])[S:3][C:4]=4[N:5]=3)[CH:13]=2)=[O:32])[CH:26]=[CH:25][CH:24]=1)([CH3:29])[CH3:28])#[N:31]

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 7764215-(propan-2-yl)-1H-pyrazole-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86646090N-{3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

생성물 1

HCID 59507053HCID 59507053, 화합물수율 32%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
90 °C

실험 절차

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (82 mg, 185 μmol) produced in Example D25(iii) in pyridine (3 mL) were added 5-(1-methylethyl)-1H-pyrazole-3-carboxylic acid (57 mg, 370 μmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (211 mg, 555 μmol), and the mixture was stirred at 90° C. for 21 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (15 mL), and the mixture was extracted with ethyl acetate (20 mL, 5 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→92/8), and the fractions containing the object product were concentrated under reduced pressure. The obtained residue was recrystallized from N,N-dimethylformamide and diethyl ether to give the title compound (34 mg, 32%) as pale-yellow crystals.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (20 mL, 5 mL)
  2. washThe combined organic layer was washed with saturated brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→92/8)
  7. additionthe fractions containing the object product
  8. concentrationwere concentrated under reduced pressure
  9. customThe obtained residue was recrystallized from N,N-dimethylformamide and diethyl ether

출처 및 근거

ORD 기록
ord-956ef2eb3edf4a6996886d8b278396a3
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

반응 노트

불러오는 중…