Trifluoroacetic acid → Mivavotinib

HRID 516000노트

반응식

HRID 516000 반응식
[F:1][C:2]1[C:3]2[CH2:31][NH:30][C:29](=[O:32])[C:4]=2[C:5]([C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15]C(=O)OC(C)(C)C.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].[NH2:15][C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]1[NH:8][C:7]1[N:6]=[C:5]([C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)[C:4]2[C:29](=[O:32])[NH:30][CH2:31][C:3]=2[C:2]=1[F:1]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 86654710tert-butyl (1S,2R)-2-(7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

생성물 2

HCID 6422Trifluoroacetic acidHCID 53252276Mivavotinib수율 60.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl (1S,2R)-2-(7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (15 mg, 0.034 mmol) and TFA (0.5 mL, 6.49 mmol) in DCM (0.5 mL) was stirred at RT for 30 min. The reaction mixture was concentrated and the resulting residue was purified by preparative HPLC to give a TFA salt of the title compound (7 mg, 60.2%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.37-2.01 (m, 8 H), 3.67 (br s, 1 H), 3.89 (s, 3 H), 4.32-4.43 (m, 2 H), 4.45 (br s, 1 H), 6.77 (d, J=6.35 Hz, 1 H), 7.93 (br s, 3 H), 8.30 (s, 1 H), 8.36 (s, 1 H), 8.84 (s, 1 H). [M+H] calc'd for C17H21FN6O, 345; found, 345.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-fc4809769d624734aaf202fd3f44b453
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108970B2

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