Water → HCID 10151423, compound

HRID 1244720Notes

Reaction equation

HRID 1244720 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[NH:11][C:12]([C:14]1[NH:18][C:17]2[C:19]([Cl:23])=[C:20]([Cl:22])[S:21][C:16]=2[CH:15]=1)=[O:13].C(N(CC)CC)C.[Cl:31][CH2:32][C:33](Cl)=[O:34].O>ClCCl>[Cl:22][C:20]1[S:21][C:16]2[CH:15]=[C:14]([C:12]([NH:11][C@@H:3]3[CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C@H:2]3[NH:1][C:33](=[O:34])[CH2:32][Cl:31])=[O:13])[NH:18][C:17]=2[C:19]=1[Cl:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chloride2×HCID 8471Triethylamine2×HCID 11772963HCID 11772963, compound

Product 1

HCID 10151423HCID 10151423, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(1R,2R)-1-Amino-2,3-dihydro-1H-inden-2-yl]-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide (Method 8, 602 mg, 1.6 mmol) was dissolved in dichloromethane (30 mL), to this was added triethylamine (0.25 mL, 1.8 mmol) and chloroacetyl chloride (0.14 mL, 1.8 mmol). The solution was stirred at ambient temperature for 16 hours, after which triethylamine (0.25 ml, 1.8 mmol) and chloroacetyl chloride (0.14 ml, 1.8 mmol) were added before stirring for 1 hour. To the resulting slurry, water (15 mL) was added before filtering to give the title product (532 mg, 73%) as a cream solid.

Workup

  1. stirringbefore stirring for 1 hour
  2. filtrationbefore filtering

Sources & evidence

ORD record
ord-2d3bacdacc5e4c1faaa2f47e2cc86d2a
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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