Trifluoroacetic acid → Mivavotinib

HRID 711465ノート

反応式

HRID 711465 の反応式
[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]

参加物

5

反応物 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

生成物 2

HCID 6422Trifluoroacetic acidHCID 53252276Mivavotinib収率 60.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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, 8H), 3.67 (br s, 1H), 3.89 (s, 3H), 4.32-4.43 (m, 2H), 4.45 (br s, 1H), 6.77 (d, J=6.35 Hz, 1H), 7.93 (br s, 3H), 8.30 (s, 1H), 8.36 (s, 1H), 8.84 (s, 1H). [M+H] calc'd for C17H21FN6O, 345. found, 345.

後処理

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

出典と根拠

ORDレコード
ord-e70c2ad71b0745b1ac4923e032569e88
出典データセット
uspto-grants-2015_11
特許番号
US09181255B2

反応ノート

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