Water → Methyl 2-(1H-indazol-6-ylamino)-6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyanonicotinate

HRID 711448

반응식

HRID 711448 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[N:20]=[C:19](Cl)[CH:18]=[C:17]([C:22]#[N:23])[C:12]=3[C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[CH:3]=[N:2]1.[NH2:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C@@H:26]1[NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].CCN(CC)CC.O>C1COCC1.CCOC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11]3[N:20]=[C:19]([NH:24][C@@H:25]4[CH2:30][CH2:29][CH2:28][CH2:27][C@@H:26]4[NH:31][C:32]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:38])[CH:18]=[C:17]([C:22]#[N:23])[C:12]=3[C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[CH:3]=[N:2]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 58317650Methyl 2-(1H-indazol-6-ylamino)-6-chloro-4-cyanonicotinate

생성물 1

HCID 67238712Methyl 2-(1H-indazol-6-ylamino)-6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyanonicotinate수율 62%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 2-(1H-indazol-6-ylamino)-6-chloro-4-cyanonicotinate (115 mg, 0.351 mmol), tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (90 mg, 0.421 mmol) and Et3N (0.073 mL, 0.526 mmol) in THF (1 mL) was stirred at reflux overnight. Water and EtOAc were added to the mixture. The aqueous phase was extracted with EtOAc. The organic phases were combined, washed with H2O and brine, dried over MgSO4, and evaporated. The residue was rinsed with EtOAc to give the title compound as yellow solid (110 mg, 62.0%). 1H NMR (500 MHz, CDCl3) δ ppm 1.00-1.86 (m, 17H), 3.84 (s, 3H), 3.91 (br s, 1H), 4.12 (br s, 1H), 6.51 (s, 1H), 6.63 (d, J=8.79 Hz, 1H), 7.13 (d, J=8.30 Hz, 1H), 7.97 (s, 1H), 8.03 (br s, 1H), 10.71 (br s, 1H), 12.87 (br s, 1H).

후처리

  1. temperatureat reflux overnight
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. washThe residue was rinsed with EtOAc

출처 및 근거

ORD 기록
ord-3c0a00146f804a8c9b20b034629d470f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

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