5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one → HCID 44181586, compound

HRID 876915Notes

Reaction equation

HRID 876915 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[N:3]=1.[O:21]=[C:22]1[NH:26][C:25]2[CH:27]=[CH:28][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:30][C:24]=2[NH:23]1>>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:28]3[CH:29]=[CH:30][C:24]4[NH:23][C:22](=[O:21])[NH:26][C:25]=4[CH:27]=3)[N:7]=[C:6]3[N:8]([CH3:11])[N:9]=[CH:10][C:5]=23)[CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 462617946-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 44181586HCID 44181586, compound

Procedure

6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6 was reacted with 2-oxo-2,3-dihydro-1H-benzoimidazole-5-boronic acid pinacol ester using General Procedure A. Purification on silica yielded 115. NMR: (CDCl3): 3.84 (s, CH3), 4.01 (s, CH3), 6.72 (dd, H, ArH, J=2.1, 8.28), 7.04 (d, H, ArH, J=8.2), 7.35 (t, H, ArH, J=8), 7.47 (d, H, ArH, J=8), 7.72 (s, H, NH), 8.06 (s, H, NH), 8.18 (dd, H, ArH, J=1.4, 8.3), 8.25 (s, H, NH), 10.03 (s, H, ArH), 10.81 (s, H, ArH), 10.86 (s, H, ArH). MS: (ESI+) MH+=388.21

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-561168e86db2453a8c520828edfaa9f1
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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