Dimethylcarbamoyl Chloride → HCID 18914265, compound

HRID 1292399Notes

Reaction equation

HRID 1292399 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=1)=[C:5]2[CH2:19][CH2:20][N:21]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=1.[CH3:44][N:45]([CH3:49])[C:46](Cl)=[O:47].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:37]([N:21]([CH2:20][CH2:19][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:46]([N:45]([CH3:49])[CH3:44])=[O:47])[CH:3]=2)[NH:7][C:6]=1[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=1)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 57227654HCID 57227654, compound

Product 1

HCID 18914265HCID 18914265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-{4-[4-({2-[5-amino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}benzylamino)butyl]phenyl}methanesulfonamide (15 mg in 1.5 mL of dry methylene chloride) at 0° C. was added dimethylcarbamyl chloride (0.03 mL of a 10% v/v solution in methylene chloride) and diisopropylethylamine (0.053 mL of a 10% v/v solution in methylene chloride) and the mixture warmed to room temperature. After 3 days the reaction was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:4:1) to give the title compound (17 mg).

Workup

  1. concentrationAfter 3 days the reaction was concentrated in vacuo
  2. custompurified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:4:1)

Sources & evidence

ORD record
ord-e6be0e07621e44809f9421b8a28003b2
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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