N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-chloro-1,3-benzoxazol-2-amine → Rac-n2-(4-{4-amino-1-[1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-chloro-1,3-benzoxazol-2-amine monoacetate

HRID 897954Notes

Reaction equation

HRID 897954 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]([CH2:17][CH2:18][O:19][CH3:20])[CH2:13]2)[N:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]3[O:37][C:38]4[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:39]=4[N:40]=3)=[CH:31][CH:30]=2)[O:23]1.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>>[C:18]([OH:19])(=[O:23])[CH3:17].[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]([CH2:17][CH2:18][O:19][CH3:20])[CH2:13]3)[N:3]=[C:2]([C:29]3[CH:30]=[CH:31][C:32]([NH:35][C:36]4[O:37][C:38]5[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:39]=5[N:40]=4)=[CH:33][CH:34]=3)[C:10]=12

Participants

4

Reactant 3

HCID 22346666N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-chloro-1,3-benzoxazol-2-amineHCID 69203235Rac-3-iodo-1-[1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-4-amineHCID 178480969HCID 178480969, compound

Product 1

HCID 69778923Rac-n2-(4-{4-amino-1-[1-(2-methoxyethyl)tetrahydro-1h-3-pyrrolyl]-1h-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-chloro-1,3-benzoxazol-2-amine monoacetate

Procedure

rac-N2-(4-{4-Amino-1-[1-(2-methoxyethyl)tetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-chloro-1,3-benzoxazol-2-amine monoacetate was prepared from rac-3-iodo-1-[1-(2-methoxyethyl)tetrahydro-1H-3-pyrrolyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.200 g, 0.319 mmol) and N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-chloro-1,3-benzoxazol-2-amine (0.148 g, 0.399 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 an off-white solid (0.080 g, 50%). 1H NMR (DMSO-d6, 400 MHz) 1.91 (s, 3H), 2.33 (m, 2H), 2.66 (m, 2H), 2.75-2.85 (m, 3H), 3.17 (t, 1H), 3.24 (s, 3H), 3.45 (t, 2H), 5.37 (m, 1H), 7.18 (d, 1H), 7.55 (d, 2H), 7.68 (d, 2H), 7.92 (d, 2H), 8.24 (s, 1H), 9.80 (s, 1H); RP-HPLC Rt 11.337 min, 97% 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 505 (MH+).

Sources & evidence

ORD record
ord-aee1054974314966aaae94852d9f1954
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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