Acetyl chloride → HCID 10359342, compound

HRID 1944546Notes

Reaction equation

HRID 1944546 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH2:18][CH2:17]3)=[O:13])[CH:2]=1.C(N(CC)C(C)C)(C)C.[C:32](Cl)(=[O:34])[CH3:33]>ClCCCl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:32](=[O:34])[CH3:33])[CH2:18][CH2:17]3)=[O:13])[CH:2]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 10379416HCID 10379416, compound

Product 1

HCID 10359342HCID 10359342, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2,3-dihydro-1H-indole-5-carboxylic acid quinolin-3-ylamide (77 mg, 0.266 mmol) and N,N-diisopropylethylamine (0.060 mL, 0.345 mmol) in 1,2-dichloroethane (2 mL) was treated with acetyl chloride (0.020 mL, 0.292 mmol). The resultant solution was stirred at room temperature overnight. The solvent was evaporated and the residue was triturated in water (1 mL) and saturated aqueous sodium bicarbonate (1 mL). The product was collected by filtration, to give the product 74 mg (84%). MS: m/z 332 (MH+). 1H NMR (DMSO-d6): δ 2.21 (s, 3H), 3.24 (t, 2 H), 4.18 (t, 2 H), 7.59 (t, 1 H), 7.67 (t, 1 H), 7.89-7.98 (m, 4 H), 8.15 (d, 1 H), 8.84 (s, 1 H), 9.14 (s, 1 H) and 10.566 (s, 1 H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated in water (1 mL)
  3. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-90b2e279dfe44890a13f35c6175bc84c
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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