Acetyl chloride → HCID 69313896, compound

HRID 2219667Notes

Reaction equation

HRID 2219667 reaction equation
[CH:1]1([NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:35])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]([C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:15]=2[CH3:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[C:45](Cl)(=[O:47])[CH3:46]>ClCCl>[C:45]([CH:8]([NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH2:9][CH2:10][NH:11][C:12](=[O:35])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]([C:25](=[O:33])[C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)[C:15]=1[CH3:34])(=[O:47])[CH3:46]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 58618086HCID 58618086, compound

Product 1

HCID 69313896HCID 69313896, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.100 g (0.2 mmol) of N-(3-cyclohexylaminoprop-1-yl)-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetamide in 1 mL of anhydrous dichloromethane was added 0.04 mL (0.24 mmol) of diisopropylethyl amine followed by 0.015 mL (0.2 mmol) of acetyl chloride. The reaction was stirred at room temperature for 20 hr then diluted with more dichloromethane (2 mL). The solution was washed with dilute aqueous citric acid (1 mL) before drying (Na2SO4), filtering and evaporating. The residue was purified by preparative HPLC to give the title compound. 1H NMR (CDCl3) δ 7.68 (2H, d), 7.39 (2H, d), 7.16 (1H, bt), 6.86 (1H, d), 6.79 (1H, d), 6.61 (1H, dd), 3.75 (3H, s), 3.57 (2H, s), 3.36 (1H, bt), 3.06 (4H, m), 2.33 (3H, s), 1.96 (3H, s), 0.9-1.8 (12H, m).

Workup

  1. washThe solution was washed with dilute aqueous citric acid (1 mL)
  2. dry with materialbefore drying (Na2SO4)
  3. filtrationfiltering
  4. customevaporating
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-94f8ee516475407abf01e94d72130a0f
Source dataset
uspto-grants-2008_08
Patent number
US07414067B2

Reaction notes

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