Ether hydrochloride → HCID 131728739, compound

HRID 601520Notes

Reaction equation

HRID 601520 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:31])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[C:19]([O:29][CH3:30])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.Cl.CCOCC>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:31])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([N:23]5[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)=[C:19]([O:29][CH3:30])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 57501733HCID 57501733, compound

Product 1

HCID 131728739HCID 131728739, compoundYield 186.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

Prepare the hydrochloride salt of the free base by mixing 2-(4-chloro-phenyl)-5-(3-methoxy-4-morpholin-4-yl-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (273 mg, 0.599 mmol) in MeOH (4 mL) and adding a 1.0M HCl/ether (0.7 mL, 0.70 mmol) solution. After all solids dissolve, cool the solution to −20° C. for 4 days. Collect the white precipitate by filtration, wash with ether, and dry under vacuum to give the title compound as a white solid (275 mg, 57%). MS (ES+) 456.0 (M+1)+. 1H NMR (400 MHz, DMSO-d6): δ 8.05 (d, 2H, J=8.4 Hz), 7.62 (d, 2H, J=8.4 Hz), 7.18 (s, 1H), 7.12 (s, 1H), 7.00-6.96 (m, 1H), 5.69 (s, 1H), 4.10 (t, 2H, J=7.0 Hz), 3.86-3.80 (m, 7H), 3.27 (t, 2H, J=7.0 Hz), 3.20-3.12 (m, 4H).

Workup

  1. dissolutionAfter all solids dissolve
  2. customCollect the white precipitate
  3. filtrationby filtration
  4. washwash with ether
  5. customdry under vacuum

Sources & evidence

ORD record
ord-578ded7f6a0443129c8b8f8919140e03
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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