Chloroacetyl chloride → HCID 69546060, compound

HRID 1244728Notes

Reaction equation

HRID 1244728 reaction equation
[Cl:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([NH:12][C@@H:13]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C@H:14]3[NH:22][CH3:23])=[O:11])[NH:5][C:4]=2[C:3]=1[Cl:24].C(N(CC)CC)C.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[Cl:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([NH:12][C@@H:13]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C@H:14]3[N:22]([C:34](=[O:35])[CH2:33][Cl:32])[CH3:23])=[O:11])[NH:5][C:4]=2[C:3]=1[Cl:24]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 58717476HCID 58717476, compound

Product 1

HCID 69546060HCID 69546060, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dichloro-N-[(1R,2R)-1-(methylamino)-2,3-dihydro-1H-inden-2-yl]-4H-thieno[3,2-b]pyrrole-5-carboxamide (Method 11; 300 mg, 0.79 mmol) and triethylamine (167 μL, 1.2 mmol) was dissolved in DCM (5 mL), chloroacetyl chloride (73 μL, 0.9 mmol) added and the reaction stirred at ambient temperature for 2 hours. The volatiles were removed by evaporation under reduced pressure and EtOAc (15 mL) added. The mixture was washed with water (10 mL), brine (10 ml), dried (MgSO4) and the volatiles were removed by evaporation under reduced pressure to give the title compound (310 mg, 86%) as a pale brown foam.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure and EtOAc (15 mL)
  2. additionadded
  3. washThe mixture was washed with water (10 mL), brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7361fde640a04623bf5668c18109251c
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

Loading…