Hydrochloric Acid → HCID 67542159, compound

HRID 1808033Notes

Reaction equation

HRID 1808033 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]2[N:14]=[C:13]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][N:31]4[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][O:39][CH3:40])[CH2:33][CH2:32]4)[CH:24]=3)[N:12]=[CH:11][C:10]=2[CH2:9]1.[ClH:41].C(OCC)C>ClCCl.C(OCC)(=O)C>[ClH:41].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]2[N:14]=[C:13]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][N:31]4[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][O:39][CH3:40])[CH2:33][CH2:32]4)[CH:24]=3)[N:12]=[CH:11][C:10]=2[CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 46239653HCID 46239653, compound

Product 1

HCID 67542159HCID 67542159, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (R)-6-(2-fluorophenyl)-N-(3-(2-(4-(2-methoxyethyl)piperazin-1-yl)ethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine (5.5 g, 10.22 mmol) was dissolved in a mixed solvents of dichloromethane (30 mL) and ethyl acetate (20 mL). To this solution was added 2.5 M HCl in ethyl acetate (30 mL) slowly while stirring. After addition, the suspension was stirred at room temperature for 10 min, and then diethyl ether (300 mL) was added. Product was collected by filtration and dried at 60° C. for 24 hours to provide 6.2 g (˜93%) of final product as a yellow solid. The purity of this salt was found to be 100% at UV 254 nm by HPLC short method (2.5 min run) and 92% at UV254 by HPLC long method (20 min run). The salt was further purified as shown in the examples disclosed herein.

Workup

  1. additionAfter addition
  2. stirringthe suspension was stirred at room temperature for 10 min
  3. filtrationProduct was collected by filtration
  4. customdried at 60° C. for 24 hours

Sources & evidence

ORD record
ord-5082b320893f4d6884d8ab89c91e331d
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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