Triethylamine → HCID 22031201, compound

HRID 1792474Notes

Reaction equation

HRID 1792474 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.[NH2:20][C:21]1[S:22][CH:23]=[C:24]([CH3:26])[N:25]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH3:26][C:24]1[N:25]=[C:21]([NH:20][C:15](=[O:17])[C:14]2[CH:13]=[CH:12][C:11]([C:8]3[N:6]4[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)=[CH:19][CH:18]=2)[S:22][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 741432-Amino-4-methylthiazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22031473HCID 22031473, compound

Product 1

HCID 22031201HCID 22031201, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

159 mg of 4-(6-bromoimidazo[1,2-a]pyridin-3-yl)benzoic acid (compound in Production Example 54), 58 mg of 2-amino-4-methyl-1,3-thiazole, 243 mg benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate and 83 μL triethylamine were reacted overnight in 4 mL dichloromethane. The reaction solution was purified by an NH silica gel column, to give 100 mg of the title compound (pale yellow crystals; recrystallization solvent, ethyl acetate-methanol).

Workup

  1. customThe reaction solution was purified by an NH silica gel column

Sources & evidence

ORD record
ord-378eecc8f6da43fc94723245ce7e7e3f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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