Acetyl chloride → HCID 10127755, compound

HRID 1244715Notes

Reaction equation

HRID 1244715 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6](=[O:31])[CH2:7][NH:8][C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[NH:18][C:19]([C:21]1[NH:25][C:24]2[C:26]([Cl:30])=[C:27]([Cl:29])[S:28][C:23]=2[CH:22]=1)=[O:20]>C1COCC1>[C:1]([N:8]([CH2:7][C:6]([NH2:5])=[O:31])[C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[NH:18][C:19]([C:21]1[NH:25][C:24]2[C:26]([Cl:30])=[C:27]([Cl:29])[S:28][C:23]=2[CH:22]=1)=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 10287901HCID 10287901, compound

Product 1

HCID 10127755HCID 10127755, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (17 μL, 0.24 mmol) was added to a solution of N-{(1R,2R)-1-[(2-amino-2-oxoethyl)amino]-2,3-dihydro-1H-inden-2-yl}-2,3-dichloro-4H-thieno[3,2-b]pyrrole-5-carboxamide (Example 28, 100 mg, 0.24 mmol) in THF (10 mL). The reaction was stirred at ambient temperature for 1 h. The volatiles were removed by evaporation under reduced pressure, the residue dissolved in EtOAc (50 mL), washed with water (2×10 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure and the residue purified by column chromatography (EtOAc:isohexane 1:2) to afford the title compound (50 mg, 45%) as a white solid.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (50 mL)
  3. washwashed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe volatiles were removed by evaporation under reduced pressure
  6. customthe residue purified by column chromatography (EtOAc:isohexane 1:2)

Sources & evidence

ORD record
ord-877ddd7e68354c52afc9968ada5837d2
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

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