(5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine → 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

HRID 897933Notes

Reaction equation

HRID 897933 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13]2)[N:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33]3[O:34][C:35]4[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:36]=4[N:37]=3)=[CH:28][CH:27]=2)O1.NC1N=CN=C2N([C@H]3CC[C@@H](N4CCN(C)CC4)CC3)N=C(C3C=CC(NC4OC5C=CC=CC=5N=4)=C(F)C=3)C=12>>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH:12]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13]3)[N:3]=[C:2]([C:26]3[CH:27]=[CH:28][C:29]([NH:32][C:33]4[O:34][C:35]5[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:36]=5[N:37]=4)=[CH:30][CH:31]=3)[C:10]=12

Participants

4

Reactant 3

HCID 11581347(5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amineHCID 589553203-iodo-1-(1-methyl-pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamineHCID 178480969HCID 178480969, compound

Product 1

HCID 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

Procedure

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 was prepared from rac-3-iodo-1-(1-methyltetrahydro-1H-3-pyrrolyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.200 g, 0.581 mmol) and N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5,7-dimethyl-1,3-benzoxazol-2-amine (0.265 g, 0.726 mmol) in a manner similar to that used for the preparation of cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-fluorophenyl)-1,3-benzoxazol-2-amine. The compound was formed as a white powder (0.062 g, 23%). 1H NMR (DMSO-d6, 400 MHz) 2.39 (s, 3H), 2.32-2.40 (m, 3H), 2.40 (s, 3H), 2.75-2.80 (m, 2H), 3.08 (t, 1H), 3.26 (s, 3H), 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 10.905 min, 96% 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-4c3e1618772e4c14b200aeaaea3a9d9a
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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