Water → [(1R,2R,3S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2,3-dihydroxycyclopentyl]methyl sulfamate

HRID 1677916노트

반응식

HRID 1677916 반응식
[S:1](=[O:33])(=[O:32])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9]C(C)(C)[O:11]2)[C@H:7]([NH:15][C:16]2[CH:21]=[C:20]([NH:22][C@@H:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24]3)[N:19]=[CH:18][N:17]=2)[CH2:6]1)[NH2:2].FC(F)(F)C(O)=O.O>>[S:1](=[O:33])(=[O:32])([O:3][CH2:4][C@H:5]1[CH2:6][C@@H:7]([NH:15][C:16]2[CH:21]=[C:20]([NH:22][C@@H:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24]3)[N:19]=[CH:18][N:17]=2)[C@H:8]([OH:9])[C@@H:12]1[OH:11])[NH2:2]

참가 물질

4

반응물 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86618703[(3aR,4R,6R,6aS)-6-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl sulfamate

생성물 1

HCID 59671258[(1R,2R,3S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}-amino)-2,3-dihydroxycyclopentyl]methyl sulfamate수율 49.2%

실험 절차

A solution of [(3aR,4R,6R,6aS)-6-({6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-methyl sulfamate (60.0 mg, 0.126 mmol) was treated with a 9:1 mixture of trifluoroacetic acid in H2O (5.00 mL, 58.4 mmol) and the mixture was stirred for 10 min before being concentrated in vacuo. The crude material was purified via reverse phase C18 preparative HPLC eluting with a gradient of 5 to 70% of 0.1% FA/95% ACN/5% H2O in 0.1% FA/99% H2O/1% ACN over 16 min to afford the title compound (27.0 mg, 49%). 1H NMR (400 MHz, DMSO-d6, δ): 8.13 (s, 1H), 7.98 (s, 1H), 7.44 (s, 2H), 7.28-7.02 (m, 5H), 6.72 (bs, 1H), 5.53 (s, 1H), 5.41 (s, 1H), 4.63 (d, J=5.3 Hz, 1H), 4.09 (dd, J=5.1, 9.5 Hz, 1H), 3.97 (dd, J=7.0, 9.5 Hz, 1H), 3.81 (bs, 1H), 3.71-3.60 (m, 2H), 3.01-2.87 (m, 1H), 2.87-2.70 (m, 1H), 2.47-2.37 (m, 1H), 2.30-2.09 (m, 2H), 1.89-1.72 (m, 1H), 1.19-1.05 (m, 1H) ppm. LC/MS: Rt=1.13 min, ES+ 436 (AA standard).

후처리

  1. concentrationbefore being concentrated in vacuo
  2. customThe crude material was purified via reverse phase C18 preparative HPLC
  3. washeluting with a gradient of 5 to 70% of 0.1%
  4. customover 16 min

출처 및 근거

ORD 기록
ord-e941d36faaf24b99a8694c90a3adcd2e
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008307B2

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