Dimethylformamide → HCID 67077023, compound

HRID 2233153Notes

Reaction equation

HRID 2233153 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([NH2:24])[C:18]=2[OH:25])(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[C:28]([F:38])=[C:29]([CH:35]=[CH:36][CH:37]=1)C(N=[N+]=[N-])=O.C[N:40](C)[CH:41]=[O:42]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([NH:24][C:41]([NH:40][C:37]3[CH:36]=[CH:35][CH:29]=[C:28]([F:38])[C:27]=3[Cl:26])=[O:42])[C:18]=2[OH:25])(=[O:15])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 18373502HCID 18373502, compoundHCID 81266090HCID 81266090, compound

Product 1

HCID 67077023HCID 67077023, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1d (3.8 g, 9.7 mmol) and 3-chloro-2-fluorobenzoyl azide (1b) (2.9 g, 14.5 mmol) in 5 mL of N,N-dimethylformamide was stirred at room temperature for 18 h. The mixture was diluted with ethyl acetate and washed with water to give the crude material. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (20/80, v/v), gave 3.6 g (66%) of 1e. LC-MS (m/z) 562.8 (M+H).

Workup

  1. washwashed with water
  2. customto give the crude material
  3. customPurification by column chromatography on silica gel
  4. washeluting with ethyl acetate/hexane (20/80

Sources & evidence

ORD record
ord-a38b303c68bd467c8b8c0d98e4329c3d
Source dataset
uspto-grants-2010_05
Patent number
US07709485B2

Reaction notes

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