Dimethylformamide → HCID 22597776, compound

HRID 1760234Notes

Reaction equation

HRID 1760234 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(N=C=N[CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])C.O[N:22]1[C:26]2[CH:27]=[CH:28]C=[CH:30][C:25]=2N=N1.C(N)([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=O.CN(C=[O:43])C>ClCCl>[C:34]([O:33][C:20]([N:18]1[CH2:17][CH2:16][C:15]2[C:28](=[CH:27][C:26]([NH:22][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])=[CH:25][CH:30]=2)[CH2:19]1)=[O:43])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 77922tert-Butyl carbamateHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 22597776HCID 22597776, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chlorothiophene-2-carboxylic acid (214 mg; 1.3 mmol), ethyldimethylaminopropyl carbodiimide (250 mg; 1.3 mmol) and 1-hydroxybenzotriazole (176 mg; 1.3 mmol) in dry DMF (25 ml) was stirred at room temperature for 30 min. A solution of the N-boc amine D6 (300 mg; 1.21 mmol) in dichloromethane (5 ml) was added and the mixture kept at room temperature overnight. Work-up gave a pink gum which was chromatographed on Kieselgel 60 in 30% ethyl acetate-hexane. Combination of appropriate fractions gave the title compound as an off white solid (0.5 g).

Workup

  1. customWork-up gave a pink gum which
  2. customwas chromatographed on Kieselgel 60 in 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-81c9ff7272c64d27b97e980782b8d71a
Source dataset
uspto-grants-2005_01
Patent number
US06841560B2

Reaction notes

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