Hydrochloric Acid → HCID 69217044, compound

HRID 1394247Notes

Reaction equation

HRID 1394247 reaction equation
Cl.[CH3:2][N:3]([CH3:34])[C:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:27])[CH:12]([NH:14][C:15](=[O:26])[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH3:13])[CH2:6][CH2:5]1.C[Si](C)(C)[Cl:37]>CC(CC)=O>[ClH:37].[CH3:34][N:3]([CH3:2])[C:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:27])[CH:12]([NH:14][C:15](=[O:26])[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH3:13])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 69217045N-(4-dimethylamino-4-phenylcyclohexyl)-2-(2-1H-indol-3-ylacetylamino)propionamide

Product 1

HCID 69217044HCID 69217044, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In order to produce the hydrochloride (Example 14), the more polar diastereomer of N-(4-dimethylamino-4-phenylcyclohexyl)-2-(2-1H-indol-3-ylacetylamino)propionamide (297 mg, 0.66 mmole) was dissolved in ethyl methyl ketone and combined with trimethylchlorosilane (125 μl, 0.99 mmole). The resulting solid was filtered out and dried. Example 14 was obtained as a colorless solid (m.p. 30-32° C.) in a yield of 200 mg (63%).

Workup

  1. filtrationThe resulting solid was filtered out
  2. customdried

Sources & evidence

ORD record
ord-a254ca815bb9487ba6f1bb938283881d
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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