(R)-3-Pyrrolidinol → n2-(4-{4-Amino-1-[(3s)-1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine monoacetate

HRID 897950Notes

Reaction equation

HRID 897950 reaction equation
N1C[CH2:4][C@@H:3]([OH:6])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]([CH2:40][CH2:41][O:42][CH3:43])[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>>[C:3]([OH:6])(=[O:25])[CH3:4].[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]([CH2:40][CH2:41][O:42][CH3:43])[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 2759337(R)-3-PyrrolidinolHCID 22347170Rac-n2-(4-{4-amino-1-[1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine

Product 1

HCID 20817160n2-(4-{4-Amino-1-[(3s)-1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine monoacetate

Procedure

N2-(4-{4-Amino-1-[(3S)-1-(2-methoxyethyl)tetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5,7-dimethyl-1,3-benzoxazol-2-amine monoacetate was prepared from (R)-(+)-3-pyrrolidinol in a manner analogous to that used for the preparation of rac-N2-(4-{4-amino-1-[1-(2-methoxyethyl)tetrahydro-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 pink solid (0.103 g, 53%). 1H NMR (DMSO-d6, 400 MHz) 1.89 (s, 3H), 2.28-2.31 (m, 2H), 2.35 (s, 3H), 2.40 (s, 3H), 2.65 (t, 2H), 2.73-2.87 (m, 2H), 3.17 (t, 2H), 3.24 (s, 3H), 3.45 (t, 2H), 5.37 (m, 1H), 6.79 (s, 1H), 7.11 (s, 1H), 7.66 (d, 2H), 7.93 (d, 2H), 8.24 (s, 1H), 10.59 (s, 2H); RP-HPLC Rt 11.607 min, 95% 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 499 (MH+).

Sources & evidence

ORD record
ord-2b425744a1e54e3c898d1b92e1864fac
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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