Carbon Dioxide → HCID 67148145, compound

HRID 2426060Notes

Reaction equation

HRID 2426060 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Cl:29])[C:5]([O:27][CH3:28])=[C:6]([CH:8]([C:10]2[C:11]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:12]([NH2:22])[CH:13]=[C:14]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[CH:15]=2)[CH3:9])[CH:7]=1.C(=O)=O.CO.Cl>ClCCl>[ClH:29].[F:1][C:2]1[CH:3]=[C:4]([Cl:29])[C:5]([O:27][CH3:28])=[C:6]([CH:8]([C:10]2[C:11]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:12]([NH2:22])[CH:13]=[C:14]([N:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[CH:15]=2)[CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 887MethanolHCID 67147660HCID 67147660, compound

Product 1

HCID 67148145HCID 67148145, compoundYield 167.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-(5-Fluoro-2-methoxy-3-chlorophenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine (70 mg, 0.15 mmol) was dissolved in dichloromethane (1.5 mL). The solution was cooled in a bath with dry ice and methanol. Hydrochloric acid (1.0 mL, 2.0 M in ether) was added slowly. The mixture was warmed to room temperature. The precipitate was filtered and washed with diethyl ether gave (1-(5-Fluoro-2-methoxy-3-chlorophenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine hydrochloride salt as a white solid (60 mg, 84%): 1H NMR (400 MHz, CD3OD): δ 7.54 (d, 1H), 7.04 (m, 2H), 6.39 (d, 1H), 6.55 (s, 1H), 4.88 (m, 1H), 4.84 (bs, 3H), 3.88 (s, 3H), 3.41 (m, 4H), 3.21 (m, 4H), 1.59 (d, 3H). MS (ESI) m/z: Calculated: 441.13; Observed: 442.2 (M+H+); (C20H25ClFN3O3S.HCl).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6baf09fecc964c78baede7378defb28c
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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