Acetyl chloride → HCID 24886521, compound

HRID 722267Notes

Reaction equation

HRID 722267 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:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[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:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 24886759HCID 24886759, compound

Product 1

HCID 24886521HCID 24886521, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (20 μL, 0.32 mmol) was added to a solution of N-{(1R,2R)-1-[(2-amino-2-oxoethyl)amino]-2,3-dihydro-1H-inden-2-yl}-5-chloro-1H-indole-2-carboxamide (Example 27, 122 mg, 0.32 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 to afford the title compound (40 mg, 29%) as a white solid.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure the residue
  2. dissolutiondissolved 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

Sources & evidence

ORD record
ord-4826dbde48e24514bc62a413d1b15103
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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