N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazol-2-amine → N1-[2-(dimethylamino)ethyl]-2-{4-amino-3-[4-(1,3-benzoxazol-2-ylamino)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}propanamide

HRID 897923Notes

Reaction equation

HRID 897923 reaction equation
[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][NH:5][C:6](=[O:37])[CH:7]([N:9]1[C:13]2=[N:14][CH:15]=[N:16][C:17]([NH2:18])=[C:12]2[C:11]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]3[O:27][C:28]4[C:34](C)=[CH:33][C:32](C)=[CH:31][C:29]=4[N:30]=3)=[CH:21][CH:20]=2)=[N:10]1)[CH3:8].O1C2C=CC=CC=2N=C1NC1C=CC(B2OC(C)(C)C(C)(C)O2)=CC=1>>[CH3:38][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6](=[O:37])[CH:7]([N:9]1[C:13]2=[N:14][CH:15]=[N:16][C:17]([NH2:18])=[C:12]2[C:11]([C:19]2[CH:20]=[CH:21][C:22]([NH:25][C:26]3[O:27][C:28]4[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=4[N:30]=3)=[CH:23][CH:24]=2)=[N:10]1)[CH3:8]

Participants

3

Reactant 2

HCID 22346815N-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazol-2-amineHCID 22346906N1-[2-(dimethylamino)ethyl]-2-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanamide

Product 1

HCID 22346995N1-[2-(dimethylamino)ethyl]-2-{4-amino-3-[4-(1,3-benzoxazol-2-ylamino)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}propanamide

Procedure

The procedure described in the preparation of N1-[2-(dimethylamino)ethyl]-2-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanamide was employed, except that the Suzuki coupling procedure employed N-(1,3-benzoxazol-2-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine. Purification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min using an 8μ Hypersil HS C18, 250×21 mm column, Rt 5.5-7.0 min) afforded N1-[2-(dimethylamino)ethyl]-2-{4-amino-3-[4-(1,3-benzoxazol-2-ylamino)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl}propanamide as an off-white solid (0.003 g, 0.006 mmol); RP-HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a 5μ Hypersil HS C18, 250×4.6 mm column) Rt 6.70 min;

Workup

  1. customPurification of the product by preparative HPLC (25 to 100% acetonitrile in 0.1 M aqueous ammonium acetate over 20 min at 21 mL/min

Sources & evidence

ORD record
ord-320af801a8414cdaa3a5ab4920df03e8
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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