5-Chloro-2-thiophenecarboxylic acid → HCID 59260114, compound

HRID 642992Notes

Reaction equation

HRID 642992 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[I:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]([CH3:24])[CH:19]=[C:20]([CH2:22][NH2:23])[N:21]=2)=[CH:13][CH:12]=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>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:23][CH2:22][C:20]2[N:21]=[C:17]([C:14]3[CH:15]=[CH:16][C:11]([I:10])=[CH:12][CH:13]=3)[N:18]([CH3:24])[CH:19]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59260093HCID 59260093, compound

Product 1

HCID 59260114HCID 59260114, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-thiophene-2-carboxylic acid (23 mg, 0.14 mmol), (2-(4-iodophenyl)-1-methyl-1H-imidazol-4-yl)methyl amine prepared above (21 mg, 0.067 mmol) and TEA (0.050 mL, 0.36 mmol) in DMF (2 mL) was added BOP (70 mg, 0.16 mmol). The mixture was stirred at room temperature overnight. It was then purified by HPLC to give 5-chloro-N-((2-(4-iodophenyl)-1-methyl-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (14 mg). MS 457.9 and 459.9 (M+H).

Workup

  1. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-e111647986644c0688b592a058f7adc6
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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