Trifluoroacetic acid → Trifluoroacetic acid

HRID 711583ノート

反応式

HRID 711583 の反応式
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]

参加物

4

反応物 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

生成物 2

HCID 6422Trifluoroacetic acid収率 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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a2512b079f34985af5bf9f0a075d4ec
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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