(3S)-pyrrolidin-3-ol → n2-(4-{4-Amino-1-[(3r)-1-methyltetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine

HRID 898032Notes

Reaction equation

HRID 898032 reaction equation
N1CC[C@H](O)C1.[NH2:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]2[N:14]([CH:35]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36]3)[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]4[O:25][C:26]5[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:27]=5[N:28]=4)=[CH:19][CH:18]=3)[C:9]=12>>[NH2:7][C:8]1[N:13]=[CH:12][N:11]=[C:10]2[N:14]([C@@H:35]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36]3)[N:15]=[C:16]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24]4[O:25][C:26]5[C:32]([CH3:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:27]=5[N:28]=4)=[CH:21][CH:22]=3)[C:9]=12

Participants

3

Reactant 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 22347063Rac-n2-{4-[4-amino-1-(1-methyltetrahydro-1h-3-pyrrolyl)-1h-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl}-5,7-dimethyl-1,3-benzoxazol-2-amine

Product 1

HCID 20817159n2-(4-{4-Amino-1-[(3r)-1-methyltetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine

Procedure

N2-(4-{4-amino-1-[(3R)-1-methyltetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine was prepared from (S)-(−)-3-pyrrolidinol in a manner analogous to that used for the preparation of rac-N2-{4-[4-Amino-1-(1-methyltetrahydro-1H-3-pyrrolyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl}-5,7-dimethyl-1,3-benzoxazol-2-amine. The compound was formed as a white solid (0.195 g, 53%). 1H NMR (DMSO-d6, 400 MHz) 1H NMR (DMSO-d6, 400 MHz) 2.31-2.35 (m, 2H), 2.32 (s, 3H), 2.35 (s, 3H), 2.40 (s, 3H), 2.70-2.77 (m, 3H), 3.05 (t, 1H), 5.40 (m, 1H), 6.80 (s, 1H), 7.11 (s, 1H), 7.66 (d, 2H), 7.93 (d, 2H), 8.24 (s, 1H), 10.85 (s, 1H); RP-HPLC Rt 11.090 min, 99% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); m/z 455 (MH+).

Sources & evidence

ORD record
ord-54d1affa30724eb18d88f07fa6ec7a51
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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