Trifluoroacetic acid → Trifluoroacetic acid

HRID 711583노트

반응식

HRID 711583 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]3[CH2:22][CH2:21][O:20][CH2:19][C@@H:18]3[NH:23]C(=O)OC(C)(C)C)[N:10]=[C:9]([C:31]3[S:32][C:33]([CH3:36])=[CH:34][CH:35]=3)[C:8]=2[C:7]1=[O:37].[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>>[NH2:23][C@@H:18]1[C@H:17]([NH:16][C:11]2[N:10]=[C:9]([C:31]3[S:32][C:33]([CH3:36])=[CH:34][CH:35]=3)[C:8]3[C:7](=[O:37])[NH:6][CH2:14][C:13]=3[C:12]=2[F:15])[CH2:22][CH2:21][O:20][CH2:19]1.[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86654747tert-Butyl (3R,4R)-4-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(5-methylthiophen-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)tetrahydro-2H-pyran-3-ylcarbamate

생성물 2

HCID 6422Trifluoroacetic acid수율 74%HCID 532510096-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(5-methylthiophen-2-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

실험 절차

A solution of tert-butyl (3R,4R)-4-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(5-methylthiophen-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (31 mg, 0.051 mmol) in TFA (10 mL) was heated to 80° C. for 1 h. After the solvent was removed, the residue was dissolved in MeOH and DCM (8 mL) and was purified via preparative HPLC eluting with water (0.05% TFA) and ACN (15-30% gradient, 0.035% TFA). The collected fractions were combined and the solvent was stripped to dryness via rotary evaporation to give the title compound as a TFA salt (13.5 mg, 74%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.78 (d, J=13.18 Hz, 1H), 2.03-2.18 (m, 1H), 2.46 (s, 3H), 3.17 (d, J=4.88 Hz, 1H), 3.55-3.65 (m, 1H), 3.75 (d, J=13.18 Hz, 1H), 3.85 (br s, 1H), 3.96-4.06 (m, 2H), 4.41 (d, J=7.81 Hz, 2H), 6.84 (d, J=2.44 Hz, 1H), 7.22 (d, J=4.88 Hz, 1H), 7.92 (br s, 2H), 8.47 (s, 1H), 8.83 (d, J=3.42 Hz, 1H). [M+H] calc'd for C17H19FN4O2S, 363. found, 363.

후처리

  1. customAfter the solvent was removed
  2. dissolutionthe residue was dissolved in MeOH
  3. customDCM (8 mL) and was purified via preparative HPLC
  4. washeluting with water (0.05% TFA) and ACN (15-30% gradient, 0.035% TFA)
  5. customthe solvent was stripped to dryness via rotary evaporation

출처 및 근거

ORD 기록
ord-6a2512b079f34985af5bf9f0a075d4ec
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

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