5-Ethyl-1,2-oxazol-3-amine → N-(5-ethyl-1,2-oxazol-3-yl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

HRID 1748346노트

반응식

HRID 1748346 반응식
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.CN(C([O:26][N:27]1N=N[C:29]2[CH:30]=[CH:31][CH:32]=[N:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N=P1N(C)CCCN1C)(C)(C)C.C(C1ON=C(N)C=1)C>C1COCC1.CN(C=O)C>[CH2:31]([C:30]1[O:26][N:27]=[C:28]([NH:33][C:16]([C:13]2[CH:12]=[CH:11][C:10]3[CH:9]=[C:8]4[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]4[C:15]=3[CH:14]=2)=[O:18])[CH:29]=1)[CH3:32]

참가 물질

7

반응물 4

HCID 50943815-Ethyl-1,2-oxazol-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2회HCID 178480484HCID 178480484, 화합물

생성물 1

HCID 68323382N-(5-ethyl-1,2-oxazol-3-yl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide수율 5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 75 mg, 0.31 mmol) in THF (2 mL) and DMF (0.5 mL) is added HATU (128 mg, 0.34 mmol). The mixture is stirred at room temperature for 1 h, after which polystyrene bound 2-tert-butylimino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (419 mg, 0.92 mmol) is added. The mixture is stirred at room temperature for 10 min and 5-ethyl-3-aminoisoxazole (103 mg, 0.92 mmol) is added. The reaction is stirred at 60° C. for 16 h and is then cooled to room temperature. The mixture is filtered, washing with methanol and the filtrate is concentrated under reduced pressure. The residue is purified via preparative HPLC using a gradient elution from 10-90% acetonitrile/water with 0.1% TFA to obtain the title compound (5 mg, 5%). LCMS: 339.20 (M+H+). (System V1)

후처리

  1. additionis added
  2. stirringThe mixture is stirred at room temperature for 10 min
  3. stirringThe reaction is stirred at 60° C. for 16 h
  4. temperatureis then cooled to room temperature
  5. filtrationThe mixture is filtered
  6. washwashing with methanol
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified via preparative HPLC
  9. washa gradient elution from 10-90% acetonitrile/water with 0.1% TFA

출처 및 근거

ORD 기록
ord-e26dde735a28448a805e7175d4243b87
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

반응 노트

불러오는 중…