Acetic Acid → (1R,2S,3R,5S)-3-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

HRID 222168노트

반응식

HRID 222168 반응식
[C@@H:1]1([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([C@H:20]4[C@@:36](C)([OH:37])[C@@H:23]5[O:24]C(C6C=CC(OC)=CC=6)[O:26][CH2:27][C@@H:22]5[CH2:21]4)[C:13]=3[N:14]=[CH:15][N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.N[C@@H]1C2C(=CC=CC=2)CC1.O.CC(O)=O>C1COCC1>[C@@H:1]1([NH:10][C:11]2[C:12]3[CH:19]=[CH:18][N:17]([C@@H:20]4[CH2:21][C@@H:22]([CH2:27][OH:26])[C@@H:23]([OH:24])[C@H:36]4[OH:37])[C:13]=3[N:14]=[CH:15][N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 70000841-Aminoindane, (S)-HCID 66618631(4aS,6R,7R,7aR)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)-7-methylhexahydrocyclopenta[d]-[1,3]dioxin-7-ol

생성물 1

HCID 66618091(1R,2S,3R,5S)-3-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (4aS,6R,7R,7aR)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)-7-methylhexahydrocyclopenta[d]-[1,3]dioxin-7-ol (312 mg, 0.594 mmol, as prepared following the procedure in Example 1a-d, using (S)-(+)-1-aminoindan in step c) in THF (1.17 mL) and water (1.17 mL) was added AcOH (3.51 mL, 61.7 mmol) under an atmosphere of nitrogen. The mixture was stirred at rt overnight. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to afford the title compound as a white solid (182 mg, 76%). LC/MS: Rt=0.85 min, ES+ 381 (FA standard).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of 0 to 10% MeOH in DCM

출처 및 근거

ORD 기록
ord-2ae5f79e0a084b2888bc16d1c21d0be2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207177B2

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