((1R,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopent-2-en-1-yl)methyl sulfamate → ((1S,3S)-3-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl sulfamate

HRID 222175Notes

Reaction equation

HRID 222175 reaction equation
[S:1](=[O:30])(=[O:29])([O:3][CH2:4][C@@H:5]1[CH2:9][C@@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([NH:19][C@@H:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[C:13]=3[CH:12]=[CH:11]2)[CH:7]=[CH:6]1)[NH2:2]>[Pd].CCOC(C)=O>[S:1](=[O:30])(=[O:29])([O:3][CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([NH:19][C@@H:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[C:13]=3[CH:12]=[CH:11]2)[CH2:9]1)[NH2:2]

Participants

4

Reactant 1

HCID 24967723((1R,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopent-2-en-1-yl)methyl sulfamate

Product 1

HCID 58944674((1S,3S)-3-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl sulfamateYield 62.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of ((1R,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopent-2-en-1-yl)methyl sulfamate (17.3 mg, 0.0406 mmol) and 10% palladium on carbon (8.60 mg) in EtOAc (0.500 mL) was put under an atmosphere of hydrogen. After 3 h the flask was purged with nitrogen and the suspension was filtered through Celite eluting with EtOAc to afford the title compound as a white solid (10.8 mg, 62%). 1H NMR (400 MHz, CDCl3, δ): 8.36 (s, 1H), 7.36 (d, J=7.3 Hz, 1H), 7.29-7.15 (m, 3H), 7.00 (d, J=3.4 Hz, 1H), 6.33 (d, J=3.4 Hz, 1H), 5.91-5.87 (m, 1H), 5.41 (br s, 2H), 5.23-5.15 (m, 2H), 4.26 (dd, J=5.8, 9.8 Hz, 1H), 4.18 (dd, J=6.2, 9.8 Hz, 1H), 3.09-3.02 (m, 1H), 2.99-2.90 (m, 1H), 2.36-2.27 (m, 2H), 2.21-2.12 (m, 2H), 2.09-1.93 (m, 3H), 1.66-1.57 (m, 1H) ppm. LC/MS: Rt=1.24 min, ES+ 428 (FA standard).

Workup

  1. customAfter 3 h the flask was purged with nitrogen
  2. filtrationthe suspension was filtered through Celite
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-8050ee3158424e21a7d5b7870b979336
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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