Triethylamine → N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)-1H-indole-5-carboxamide

HRID 1802647Notes

Reaction equation

HRID 1802647 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]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.Cl.[NH2:48][CH2:49][C:50]1[N:51]=[CH:52][N:53]([C:55]2[CH:60]=[CH:59][C:58]([N:61]3[CH:66]=[CH:65][CH:64]=[CH:63][C:62]3=[O:67])=[CH:57][CH:56]=2)[CH:54]=1>CN(C=O)C>[O:67]=[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][N:61]1[C:58]1[CH:59]=[CH:60][C:55]([N:53]2[CH:54]=[C:50]([CH2:49][NH:48][C:10]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[NH:1][CH:2]=[CH:3]4)=[O:12])[N:51]=[CH:52]2)=[CH:56][CH:57]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 742801H-Indole-5-Carboxylic AcidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 669741011-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one hydrochloride

Product 1

HCID 24760449N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)-1H-indole-5-carboxamideYield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of indole-5-carboxylic acid (40 mg, 0.25 mmol) and triethylamine (0.150 mL, 1.08 mmol) in DMF (2 mL), BOP (135 mg, 0.30 mmol) was added. After 5 min of stirring, 1-(4-(4-(aminomethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one hydrochloride (53 mg, 0.18 mmol) was added. The mixture was stirred at room temperature overnight. It was then purified by HPLC to give the titled compound (30 mg). MS 410.2 (M+H).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-c74661b869e74c129ad016c2e6c64348
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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