Hydrochloric Acid → 2-(2-1H-Indol-3-ylacetylamino)-4-methylpentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

HRID 1394249Notes

Reaction equation

HRID 1394249 reaction equation
Cl.[CH3:2][N:3]([CH3:37])[C:4]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:30])[CH:12]([NH:17][C:18](=[O:29])[CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:6][CH2:5]1.C[Si](C)(C)[Cl:40]>CC(CC)=O>[ClH:40].[CH3:37][N:3]([CH3:2])[C:4]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:30])[CH:12]([NH:17][C:18](=[O:29])[CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 98282222-(2-1H-Indol-3-ylacetylamino)-4-methylpentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide

Product 1

HCID 98282212-(2-1H-Indol-3-ylacetylamino)-4-methylpentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In order to produce the hydrochloride (Example 16), the more polar compound of 2-(2-1H-indol-3-ylacetylamino)-4-methylpentanoic acid-(4-dimethylamino-4-phenylcyclohexyl)amide (320 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 16 was obtained as a colorless solid (m.p. 174-176° C.) in a yield of 170 mg (50%).

Workup

  1. filtrationThe resulting solid was filtered out
  2. customdried

Sources & evidence

ORD record
ord-f1167491b1b04f2f8f11cd2590a68f0d
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

Loading…