(5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine → Rac-1-[3-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1h-pyrazolo[3,4-d]pyrimidin-1-yl)tetrahydro-1h-1-pyrrolyl]-2-(dimethylamino)-1-ethanone

HRID 2056128Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:16][CH2:15][N:14]([C:17](=[O:22])[CH2:18][N:19]([CH3:21])[CH3:20])[CH2:13]3)[N:9]=[C:10](I)[C:3]=12.CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38]3[O:39][C:40]4[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:41]=4[N:42]=3)=[CH:33][CH:32]=2)O1>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:16][CH2:15][N:14]([C:17](=[O:22])[CH2:18][N:19]([CH3:21])[CH3:20])[CH2:13]3)[N:9]=[C:10]([C:31]3[CH:32]=[CH:33][C:34]([NH:37][C:38]4[O:39][C:40]5[C:46]([CH3:47])=[CH:45][C:44]([CH3:48])=[CH:43][C:41]=5[N:42]=4)=[CH:35][CH:36]=3)[C:3]=12

Participants

Reactant 2

HCID 11581347(5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine

HCID 69203801Rac-1-[3-(4-amino-3-iodo-1h-pyrazolo[3,4-d]pyrimidin-1-yl)tetrahydro-1h-1-pyrrolyl]-2-(dimethylamino)-1-ethanone

Product 1

HCID 69206249Rac-1-[3-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1h-pyrazolo[3,4-d]pyrimidin-1-yl)tetrahydro-1h-1-pyrrolyl]-2-(dimethylamino)-1-ethanone

Procedure

rac-1-[3-(4-Amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)tetrahydro-1H-1-pyrrolyl]-2-(dimethylamino)-1-ethanone was prepared from rac-1-[3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)tetrahydro-1H-1-pyrrolyl]-2-(dimethylamino)-1-ethanone (0.278 g, 0.669 mmol) and N2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5,7-dimethyl-1,3-benzoxazol-2-amine (0.305 g, 0.837 mmol) in a manner similar to that used for the preparation of cis-N-2-(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 (0.219 g, 62%). 1H NMR (DMSO-d6, 400 MHz) 2.17 (s, 3H), 2.23 (s, 3H), 2.3-2.50 (m, 4H), 2.34 (s, 3H), 2.40 (s, 3H), 2.99-4.26 (m, 4H), 5.44-5.49 (m, 1H), 6.80 (s, 1H), 7.11 (s, 1H), 7.65 (d, 2H), 7.92 (d, 2H), 8.26 (s, 1H), 10.86 (s, 1H); RP-HPLC Rt 10.765 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 526 (MH+).

Sources & evidence

ORD record: ord-3a2f84ffa92a40a6a638ab8d7a8fc2a4
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332497B2

Reaction notes

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