Potassium Carbonate → HCID 67283251, compound

HRID 1910709Notes

Reaction equation

HRID 1910709 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]3[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:17]=3[N:18]([CH3:34])[C:19](=[O:33])[CH:20]([CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)[N:21]=2)=[CH:11][N:10]=1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:39][C:37]1[CH:36]=[CH:35][C:17]2[N:18]([CH3:34])[C:19](=[O:33])[CH:20]([CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)[N:21]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])=[N:10][CH:11]=3)[C:16]=2[CH:38]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 46947037HCID 46947037, compound

Product 1

HCID 67283251HCID 67283251, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(5-(7-Chloro-1-methyl-3-(naphthalen-2-ylmethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-ylamino)-2-oxoethyl acetate (20 mg, 0.04 mmol) was dissolved in methanol (0.5 mL) and water (0.1 mL), potassium carbonate was added and the mixture was stirred at ambient temperature for 45 minutes. The crude mixture as partitioned between ethyl acetate and water, the layers were separated, and the organic layer was dried with sodium sulfate, decanted, then concentrated in the presence of silica gel. Column chromatography eluting with a step gradient of 20-80% ethyl acetate in hexanes in 5% increments every 3 minutes provided N-(5-(7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)pyridin-2-yl)-2-hydroxyacetamide (8 mg, 43% yield). ESI m/z measured 521.1348 [M+H]+. calculated 521.1356.

Workup

  1. customThe crude mixture as partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. customdecanted
  5. concentrationconcentrated in the presence of silica gel
  6. washColumn chromatography eluting with a step gradient of 20-80% ethyl acetate in hexanes in 5% increments every 3 minutes

Sources & evidence

ORD record
ord-09a9e2f5beac41abbe7b2c29b9d7f0d1
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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