(R)-2-(2-(2,4-Dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide → (R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide

HRID 711570노트

반응식

HRID 711570 반응식
COC1C=C(OC)C=CC=1C[N:6]1[CH2:14][C:13]2[C:12]([F:15])=[C:11]([NH:16][C@H:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([NH:20][CH3:21])=[O:19])[N:10]=[C:9]([C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)[C:8]=2[C:7]1=[O:32]>C(O)(C(F)(F)F)=O>[F:15][C:12]1[C:13]2[CH2:14][NH:6][C:7](=[O:32])[C:8]=2[C:9]([C:26]2[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=2)=[N:10][C:11]=1[NH:16][C@H:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([NH:20][CH3:21])=[O:19]

참가 물질

3

반응물 1

HCID 67238387(R)-2-(2-(2,4-Dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide

생성물 1

HCID 53251341(R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of (R)-2-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide (38 mg, 0.072 mmol) in TFA (5 mL) was heated to 65° C. for 4 h. After removal of the solvent, the residue was diluted in MeOH (2 mL) and was purified by preparative HPLC eluting with water (0.05% TFA) and ACN (25-30%, gradient, 0.035% TFA). The collected fractions were stripped to dryness to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.84-0.93 (m, 6H), 1.63-1.81 (m, 2H), 2.57 (d, J=4.39 Hz, 3H), 3.88 (s, 3H), 4.04-4.19 (m, 2H), 4.36 (s, 2H), 6.99 (d, J=7.32 Hz, 1H), 7.61-7.76 (m, 1H), 7.93 (d, J=4.39 Hz, 1H), 8.30 (s, 1H), 8.83 (s, 1H). [M+H] calc'd for C18H23FN6O2, 375. found, 375.

후처리

  1. customAfter removal of the solvent
  2. additionthe residue was diluted in MeOH (2 mL)
  3. customwas purified by preparative HPLC
  4. washeluting with water (0.05% TFA) and ACN (25-30%, gradient, 0.035% TFA)

출처 및 근거

ORD 기록
ord-d049de2006064850b07ecdf8ee14d5f4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

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