Carbon Dioxide → HCID 67147345, compound

HRID 1910624Notes

Reaction equation

HRID 1910624 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:29])[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.[ClH:35]>ClCCl>[ClH:35].[F:1][C:2]1[CH:3]=[C:4]([CH3:29])[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

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 887MethanolHCID 67147346HCID 67147346, compound

Product 1

HCID 67147345HCID 67147345, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-(5-Fluoro-2-methoxy-3-methylphenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine (60 mg, 0.14 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-methylphenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzenamine hydrochloride salt as a white solid (52 mg, 81%): 1H NMR (400 MHz, CD3OD): 1H NMR (400 MHz, CD3OD): δ 7.71 (d, 1H), 6.94 (dd, 1H), 6.85 (dd, 1H), 6.59 (d, 1H), 6.39 (dd, 1H), 4.95 (bs, 3H), 4.88 (m, 1H), 3.79(s, 3H), 3.34-3.15(m, 4H), 3.15 (s, 3H), 2.98 (m, 4H), 2.32 (s, 3H), 1.49 (d, 3H). MS (ESI) m/z: Calculated: 421.18; Observed: 422.2 (M+H+); (C21H28FN3O3S.HCl).

Workup

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

Sources & evidence

ORD record
ord-fb33e34185514d78ab736c0f4ec4854a
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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