Triethylamine → 5-chloro-N-((1-(4-(2-oxopiperidin-1-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide

HRID 499829Notes

Reaction equation

HRID 499829 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:44][CH2:45][C:46]1[N:47]=[CH:48][N:49]([C:51]2[CH:56]=[CH:55][C:54]([N:57]3[CH2:62][CH2:61][CH2:60][CH2:59][C:58]3=[O:63])=[CH:53][CH:52]=2)[CH:50]=1>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:44][CH2:45][C:46]2[N:47]=[CH:48][N:49]([C:51]3[CH:52]=[CH:53][C:54]([N:57]4[CH2:62][CH2:61][CH2:60][CH2:59][C:58]4=[O:63])=[CH:55][CH:56]=3)[CH:50]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 669740921-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)piperidin-2-one

Product 1

HCID 247602285-chloro-N-((1-(4-(2-oxopiperidin-1-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamideYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-thiophene-2-carboxylic acid 1-5 (43 mg, 0.26 mmol) and triethylamine (0.200 mL, 1.43 mmol) in DMF (2 mL), BOP (130 mg, 0.29 mmol) was added. After 5 min of stirring, the solution was added to a solid sample of 1-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)piperidin-2-one (54 mg, 0.18 mmol) in a flask. After being stirred at room temperature for 2 h, the mixture was purified by HPLC to give the titled compound (45 mg). MS 415.1 and 417.1 (M+H, Cl pattern).

Workup

  1. stirringAfter being stirred at room temperature for 2 h
  2. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-8827ac72d1ce4abe8d421f6bdddca93c
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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