1-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea → HCID 44547899, compound

HRID 2400362Notes

Reaction equation

HRID 2400362 reaction equation
I[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[N:13][CH:14]=[C:15]([CH3:17])[N:16]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]([NH:32][C:33]([NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[O:34])[CH:29]=[CH:30][CH:31]=2)O1>>[CH3:17][C:15]1[N:16]=[C:11]([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([C:30]4[CH:29]=[C:28]([NH:32][C:33]([NH:35][CH2:36][C:37]([F:38])([F:39])[F:40])=[O:34])[CH:27]=[CH:26][CH:31]=4)=[CH:3][N:4]=[C:5]3[CH:10]=2)[N:12]=[N:13][CH:14]=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 67029295HCID 67029295, compound

Product 1

HCID 44547899HCID 44547899, compound

Procedure

3-Iodo-7-(5-methyl-[1,2,4]triazin-3-yl)-imidazo[1,2-a]pyridine (120 mg, 0.4 mmol, 1 equiv) 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 (85 mg). 1H NMR (400 MHz, DMSO-d6): 9.34 (1H, s), 8.99 (1H, s), 8.74 (1H, d), 8.67 (1H, s), 7.98 (1H, d), 7.93 (1H, s), 7.79 (1H, s), 7.55-7.43 (2H, m), 7.31 (1H, d), 6.87 (1H, t), 3.99-3.88 (2H, m), 2.65 (3H, s). MS: [M+H]+428

Sources & evidence

ORD record
ord-50f2a0fcc6da4ec79e58a646de44ae43
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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