Hydrochloric Acid → HCID 57742466, compound

HRID 60209Notes

Reaction equation

HRID 60209 reaction equation
C([O:3][C:4]([C:6]1[CH:32]=[CH:31][CH:30]=[CH:29][C:7]=1[CH2:8][C:9]1[S:10][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[C:16]=2[N:17]=1)=[CH2:5])C.Cl>C1COCC1.CCOC(C)=O>[F:27][C:25]([F:26])([F:28])[C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:15]2[C:16]3[N:17]=[C:9]([CH2:8][C:7]4[CH:29]=[CH:30][CH:31]=[CH:32][C:6]=4[C:4](=[O:3])[CH3:5])[S:10][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68517211HCID 68517211, compound

Product 1

HCID 57742466HCID 57742466, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

{2-[2-(1-Ethoxy-vinyl)-benzyl]-thiazolo[5,4-d]pyrimidin-7-yl}-(4-trifluoromethyl-phenyl)-amine (230 mg, 0.62 mmol) was dissolved in THF (5 mL) and 2 N HCl (2 mL) and the reaction mixture was stirred at rt for 1.5 h. The reaction mixture was diluted with EtOAc (20 mL), washed with satd. aq. NaCl (2×5 mL), dried (Na2SO4), and concentrated to provide a white solid (0.23 g, 69%). MS (ESI): mass calcd. for C21H15F3N4OS, 428.4; m/z found, 429.1 [M+H]+. 1H NMR (CDCl3): 8.61 (S, 1H), 8.08 (s, 1H), 7.98 (d, J=8.5 Hz, 2H), 7.91 (dd, J=8.0, 1.2 Hz, 1H), 7.64 (d, J=8.6 Hz, 2H), 7.58-7.54 (m, 1H), 7.50-7.46 (m, 2H), 4.75 (s, 2H), 2.64 (s, 3H).

Workup

  1. washwashed with satd
  2. dry with materialaq. NaCl (2×5 mL), dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d69095ff078b45559ec35ad261818a55
Source dataset
uspto-grants-2016_09
Patent number
US09440978B2

Reaction notes

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