Triethylamine → N-Benzyloxy-1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 720538Notes

Reaction equation

HRID 720538 reaction equation
Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[F:23][C:24]1[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:25]=1[CH2:26][N:27]1[C:31]2=[CH:32][N:33]=[C:34]([C:36]([OH:38])=O)[CH:35]=[C:30]2[CH:29]=[CH:28]1.C(N(CC)CC)C.[CH2:51]([O:58][NH2:59])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CN(C=O)C.O>[CH2:51]([O:58][NH:59][C:36]([C:34]1[CH:35]=[C:30]2[CH:29]=[CH:28][N:27]([CH2:26][C:25]3[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:24]=3[F:23])[C:31]2=[CH:32][N:33]=1)=[O:38])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 102313O-BenzylhydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 218922121-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid

Product 1

HCID 10091952N-Benzyloxy-1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxamideYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-[3-(dimethylamino)propyl]-3-ethyl-carbodiimide hydrochloride (EDC, 126 mg, 0.67 mmol) and 1-hydroxybenzotriazole (HOBt, 56 mg, 0.56 mmol) was added to a the stirred solution of 1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (70 mg, 0.24 mmol) in DMF (8 mL). The mixture was stirred for 1 h, and then triethylamine (0.33 ml, 2.37 mmol) and O-benzylhydroxylamine (231 mg, 1.80 mmol) were added. The resulting mixture was stirred for 24 h at ambient temperature, and then water (50 mL) was added. The precipitates were collected, and dried to give the title compound (60 mg, 63%). 1H NMR (DMSO-d6) δ; 11.71 (s, 1H), 8.81 (s, 1H), 8.20(s, 1H), 7.74 (s, 1H), 7.15–7.45 (m, 7H), 7.02 (m, 1H), 6.68 (s, 1H), 5.60 (s, 2H), 4.88 (s, 2H). HRMS calcd for C22H18F2N3O2 (M+H) 394.1367. found 394.1388.

Workup

  1. stirringThe resulting mixture was stirred for 24 h at ambient temperature
  2. customThe precipitates were collected
  3. customdried

Sources & evidence

ORD record
ord-03a7fb7aa51342289cb6b9d5286fe033
Source dataset
uspto-grants-2006_11
Patent number
US07135482B2

Reaction notes

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