N-((3S,4S)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin-2-yl)pyrrolidin-3-yl)acrylamide → N-((3R,4R)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin-2-yl)pyrrolidin-3-yl)acrylamide

HRID 928162Notes

Reaction equation

HRID 928162 reaction equation
[F:1][C@H:2]1[CH2:6][N:5]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[CH:16]([CH3:18])[CH3:17])=[C:9]([NH:19][C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[N:8]=2)[CH2:4][C@@H:3]1[NH:26][C:27](=[O:30])[CH:28]=[CH2:29]>CCO>[F:1][C@@H:2]1[CH2:6][N:5]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[CH:16]([CH3:18])[CH3:17])=[C:9]([NH:19][C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[N:8]=2)[CH2:4][C@H:3]1[NH:26][C:27](=[O:30])[CH:28]=[CH2:29]

Participants

3

Reactant 1

HCID 118073685N-((3S,4S)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin-2-yl)pyrrolidin-3-yl)acrylamide

Product 1

HCID 118073677N-((3R,4R)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin-2-yl)pyrrolidin-3-yl)acrylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-((3S,4S)-4-fluoro-1-(9-isopropyl-6-((1-methyl-1H-pyrazol-4-yl)amino)-9H-purin -2-yl)pyrrolidin-3-yl)acrylamide, 36.7 mg, 9% yield (in 3 steps), >99% ee, 95% pure. Optical rotation: [α]D22=−19.06° (c 0.08, EtOH). 1H NMR (600 MHz, DMSO-17 mm) δ ppm 9.65 (br. s., 1 H) 8.50 (d, J=6.42 Hz, 1 H) 8.00 (s, 1 H) 7.92 (s, 1 H) 7.69 (s, 1 H) 6.19-6.29 (m, 1 H) 6.11-6.18 (m, 1 H) 5.63 (d, J=11.92 Hz, 1 H) 5.08-5.22 (m, 1 H) 4.46-4.69 (m, 2 H) 3.88 (br. s., 2 H) 3.82 (s, 3 H) 3.64-3.79 (m, 2 H) 1.50 (d, J=6.79 Hz, 6 H). m/z (APCI+) for C19H24FN9O 414.1 (M+H)+.

Sources & evidence

ORD record
ord-3c6cb97a4e914a29bc8c5ff2d3fcf331
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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