Hydrochloric Acid → 2-(4-Chloro-phenyl)-5-[3-chloro-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one hydrochloride

HRID 601552Notes

Reaction equation

HRID 601552 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:32])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)=[C:19]([Cl:31])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.Cl>CO.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:32])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)=[C:19]([Cl:31])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 114973602-(4-Chloro-phenyl)-5-[3-chloro-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

Product 1

HCID 114973592-(4-Chloro-phenyl)-5-[3-chloro-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one hydrochlorideYield 158.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Treat a solution of 2-(4-chloro-phenyl)-5-[3-chloro-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (60.0 mg, 0.12 mmol) in MeOH (2.0 mL) with 1N HCl in ether (1.0 mL). Sonicate at room temperature for 15 min, concentrate, and dry to give the title compound (50 mg, 78%). MS (ES+) 488 (M+1; free amine)+. 1H NMR (400 MHz, DMSO-d6): δ 10.44 (s, 1H), 8.02 (d, 2H, J=8.6 Hz), 7.59 (m, 2H), 7.55 (d, 1H, J=2.4 Hz), 7.36 (dd, 1H, J=8.8, 2.4 Hz), 7.25 (d, 1H, J=8.8 Hz), 4.43 (t, 2H, J=4.8 Hz), 4.05 (t, 2H, J=7.0 Hz), 3.62 (m, 4H), 3.24 (t, 2H, J=7.0 Hz), 3.14 (m, 2H), 2.01 (m, 2H), 1.86 (m, 2H).

Workup

  1. customSonicate at room temperature for 15 min
  2. concentrationconcentrate
  3. customdry

Sources & evidence

ORD record
ord-532809c594d24065a920eea4be79129b
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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