2-Methylphenyl boronic acid → HCID 178438246, compound

HRID 897925Notes

Reaction equation

HRID 897925 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:32]3[CH2:37][CH2:36][C@@H:35]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[CH2:34][CH2:33]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[S:19][C:20]([CH2:30][CH3:31])=[C:21]([C:23]5[CH:28]=[CH:27][C:26](C)=[CH:25][CH:24]=5)[N:22]=4)=[CH:13][CH:12]=3)[C:3]=12.[C:45]1(C)C=CC=CC=1B(O)O>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:32]3[CH2:33][CH2:34][C@@H:35]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[CH2:36][CH2:37]3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18]4[S:19][C:20]([CH2:30][CH3:31])=[C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[CH3:45])[N:22]=4)=[CH:15][CH:16]=3)[C:3]=12

Participants

3

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 178438248HCID 178438248, compound

Product 1

HCID 178438246HCID 178438246, compound

Procedure

The procedure described for cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-ethyl-4-(4-methylphenyl)-1,3-thiazol-2-amine was used to convert o-tolylboronic acid (0.200 g, 1.47 mmol) to the title compound. 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 9.8-11.7 min) afforded cis-N2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-ethyl-4-(2-methylphenyl)-1,3-thiazol-2-amine as an off-white solid (0.075 g, 0.123 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 9.83 min; MS (MH)+ 608.

Sources & evidence

ORD record
ord-86f544a999a1462cb45930960b554536
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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