Hydrochloric Acid → 1-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-3-methyl-1,3-dihydroimidazol-2-one hydrochloride

HRID 251881Notes

Reaction equation

HRID 251881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].Cl[C:22](OC1C=CC([N+]([O-])=O)=CC=1)=[O:23].CO[CH:36](OC)[CH2:37][NH:38][CH3:39].Cl>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:36]=[CH:37][N:38]([CH3:39])[C:22]1=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85032,2-DimethoxyethylmethylamineHCID 821294-Nitrophenyl chloroformateHCID 66864574(R)-2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine

Product 1

HCID 668653501-[2-((R)-6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-3-methyl-1,3-dihydroimidazol-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine (enantiomer B, preparation as described in WO2004085404), 4-nitrophenyl chloroformate and methylaminoacetaldehyde dimethyl acetal were reacted analogously to example 40, and the resulting intermediate (85 mg) was subsequently cyclized with a mixture of water (1 ml) and 10% hydrochloric acid (3.2 ml). Workup and purification were analogous to example 40. 65 mg of the title compound were isolated.

Workup

  1. customWorkup and purification

Sources & evidence

ORD record
ord-1898878f1a2f4ed583e04e15f8f42ce3
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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