1-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea → HCID 44547898, compound

HRID 2400357Notes

Reaction equation

HRID 2400357 reaction equation
I[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[N:13][CH:14]=[CH:15][N:16]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]([NH:31][C:32]([NH:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[O:33])[CH:28]=[CH:29][CH:30]=2)O1>>[N:13]1[CH:14]=[CH:15][N:16]=[C:11]([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([C:29]4[CH:28]=[C:27]([NH:31][C:32]([NH:34][CH2:35][C:36]([F:37])([F:38])[F:39])=[O:33])[CH:26]=[CH:25][CH:30]=4)=[CH:3][N:4]=[C:5]3[CH:10]=2)[N:12]=1

Participants

3

Reactant 2

HCID 574976911-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-ureaHCID 69088998HCID 69088998, compound

Product 1

HCID 44547898HCID 44547898, compound

Procedure

3-Iodo-7-[1,2,4]triazin-3-yl-imidazo[1,2-a]pyridine (96 mg, 0.3 mmol) and 1-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea were coupled according to procedure D4 to furnish the title compound as a yellow solid (39 mg). 1H NMR (400 MHz, Me-d3-OD & CDCl3): 9.26 (1H, d), 8.91-8.80 (2H, m), 8.67 (1H, d), 8.16-8.04 (2H, m), 7.85 (2H, d), 7.48 (1H, t), 7.39 (1H, d), 7.30 (1H, d), 3.91 (2H, q). MS: [M+H]+414

Sources & evidence

ORD record
ord-df00d61ac7e744e0b85879b0062af064
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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