Chloroacetyl chloride → methyl 2-{3-(acetylamino)-2-[(chloroacetyl)amino]phenyl}-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1518230Notes

Reaction equation

HRID 1518230 reaction equation
CN1CCOCC1.[Cl:8][CH2:9][C:10](Cl)=[O:11].[C:13]([NH:16][C:17]1[C:18]([NH2:42])=[C:19]([C:23]2[NH:24][C:25]3[C:30]([C:31]=2[CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:29][CH:28]=[C:27]([C:38]([O:40][CH3:41])=[O:39])[CH:26]=3)[CH:20]=[CH:21][CH:22]=1)(=[O:15])[CH3:14]>C(Cl)Cl>[C:13]([NH:16][C:17]1[C:18]([NH:42][C:10](=[O:11])[CH2:9][Cl:8])=[C:19]([C:23]2[NH:24][C:25]3[C:30]([C:31]=2[CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:29][CH:28]=[C:27]([C:38]([O:40][CH3:41])=[O:39])[CH:26]=3)[CH:20]=[CH:21][CH:22]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 79724-Methylmorpholine2×HCID 68708755methyl 2-[3-(acetylamino)-2-aminophenyl]-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 68706281methyl 2-{3-(acetylamino)-2-[(chloroacetyl)amino]phenyl}-3-cyclohexyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-methyl morpholine (1 eq) and chloroacetylchloride (1 eq) were added to a stirred solution of methyl 2-[3-(acetylamino)-2-aminophenyl]-3-cyclohexyl-1H-indole-6-carboxylate in CH2Cl2 (0.03 M) under N2. After stirring at RT for 1 h, further N-methyl morpholine (1 eq) and chloroacetylchloride (1 eq) were introduced. The reaction was stirred for another hour before diluting with CH2Cl2 and washing with 1N HCl (aq), water and brine. The organics were then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a brown solid that was taken on in the subsequent step without further purification (91%). MS (ES+) m/z 482 (M+H)+, 484 (M+H)+.

Workup

  1. stirringThe reaction was stirred for another hour
  2. washwashing with 1N HCl (aq), water and brine
  3. dry with materialThe organics were then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba0b26d486c540ca96476c13b530c1d4
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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