Hydrochloric Acid → HCID 68695991, compound

HRID 646101Notes

Reaction equation

HRID 646101 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:28][CH:27]=2)[C:8]2[C:13]([CH:14]=1)=[C:12]([NH2:15])[C:11]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[C:36](Cl)(=[O:38])[CH3:37].CCN(CC)CC.Cl>CC#N>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:34])[CH3:35])=[CH:28][CH:27]=2)[C:8]2[C:13]([CH:14]=1)=[C:12]([NH:15][C:36](=[O:38])[CH3:37])[C:11]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][CH:21]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68696976HCID 68696976, compound

Product 1

HCID 68695991HCID 68695991, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-amino-1,5-bis(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (160 mg, 0.34 mmol; see Example 5(a)), acetyl chloride (50 mg, 0.63 mmol), Et3N (63 mg, 0.63 mmol) and MeCN (10 mL) was stirred at room temperature for 30 minutes, then poured into HCl (1M) and extracted with EtOAc. The combined extracts were washed with water and brine, and dried over Na2SO4. Concentration and purification by chromatography gave the sub-title compound (182 mg, 84%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration and purification by chromatography

Sources & evidence

ORD record
ord-dce961c218a04396a3a1ef672e9db212
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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