Hydrochloric Acid → HCID 11519171, compound

HRID 601540Notes

Reaction equation

HRID 601540 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:33])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)=[C:19]([O:31][CH3:32])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.Cl>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:33])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)=[C:19]([O:31][CH3:32])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11519172HCID 11519172, compound

Product 1

HCID 11519171HCID 11519171, compoundYield 161.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mix 2-(4-chloro-phenyl)-5-[3-methoxy-4-(3-pyrrolidin-1-yl-propyl)-phenyl]-5H-thiazolo[5,4-c]pyridin-4-one (833 mg, 1.74 mmol) in MeOH (10 mL) and add 1N HCl (2.0 mL, 2.0 mmol). Stir the mixture at room temperature until all the solids dissolve then cool to −20° C. overnight. Collect the precipitate by filtration, wash with ether, and dry under vacuum to give the title compound (725 mg, 81%). MS (ES+) 480.0 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 10.14 (s, 1H), 8.16 (d, 2H, J=8.8 Hz), 7.77 (d, 1H, J=7.5 Hz), 7.67 (d, 2H, J=8.8 Hz), 7.34 (d, 1H, J=8.4 Hz), 7.15 (d, 1H, J=1.8 Hz), 7.09-7.02 (m, 2H), 3.83 (s, 3H), 3.58-3.50 (m, 2H), 3.20-3.13 (m, 2H), 3.02-2.94 (m, 2H), 2.68 (t, 2H, J=7.7 Hz), 2.03-1.93 (m, 4H), 1.90-1.83 (m, 2H).

Workup

  1. dissolutiondissolve
  2. temperaturethen cool to −20° C. overnight
  3. customCollect the precipitate
  4. filtrationby filtration
  5. washwash with ether
  6. customdry under vacuum

Sources & evidence

ORD record
ord-136d5eda39ab4a4ead700bb65c19a86a
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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