Dimethylformamide → HCID 12132338, compound

HRID 2415782Notes

Reaction equation

HRID 2415782 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:15]2[O:14][CH2:13][CH2:12][CH2:11][O:10][C:9]=2[CH:8]=[C:7]([NH2:16])[CH:6]=1)=[O:4].[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([C:27](O)=[O:28])=[CH:21]2.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C=O)C>O>[CH3:1][O:2][C:3]([C:5]1[C:15]2[O:14][CH2:13][CH2:12][CH2:11][O:10][C:9]=2[CH:8]=[C:7]([NH:16][C:27]([C:22]2[NH:23][C:24]3[C:20]([CH:21]=2)=[CH:19][C:18]([Cl:17])=[CH:26][CH:25]=3)=[O:28])[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57588233HCID 57588233, compound

Product 1

HCID 12132338HCID 12132338, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-Amino-3,4-dihydro-2H-benzo[b][1,4]dioxepine-6-carboxylic acid methyl ester (0.300 g), 5-Chloro-1H-Indole-2-carboxylic acid (0.263 g), BOP (0.594), TEA (0.377 mL) and DMF (3.0 mL) were mixed together and stirred for 4 hours. The reaction was diluted with water and the resulting filtrate filtered. The resulting solid was tritriated with EtOAc, rinished with the same and purified by flash chromatography (silica gel; 25% EtOAc/hexane) to yield 122 mg of the product. MS PDS: M+ 401/403

Workup

  1. filtrationthe resulting filtrate filtered
  2. custompurified by flash chromatography (silica gel; 25% EtOAc/hexane)

Sources & evidence

ORD record
ord-a0e606a4b3ac43059efae81bf25959c0
Source dataset
uspto-grants-2004_11
Patent number
US06821977B2

Reaction notes

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