Hydrochloric Acid → HCID 60209470, compound

HRID 1989651Notes

Reaction equation

HRID 1989651 reaction equation
CN(C)C=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)[CH:19]=[C:18]([CH3:32])[N:17]=3)[CH:11]=2)[N:9]=1.Cl.[OH-].[Na+]>C1COCC1>[CH3:32][C:18]1[N:17]=[C:16]([C:12]2[CH:11]=[C:10]([C:8]3[N:9]=[C:5]([NH2:4])[S:6][CH:7]=3)[CH:15]=[CH:14][CH:13]=2)[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68690954HCID 68690954, compound

Product 1

HCID 60209470HCID 60209470, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above described N,N-dimethyl-N′-(4-{3-[6-methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-phenyl}-thiazol-2-yl)-formamidine (880 mg, 1.886 mmol) was treated with 3 M HCl (20 mL) in THF (20 mL) at 50° C. for 16 h. Added 2 N NaOH until pH 10 was reached, extracted twice with EtOAc, dried combined organic layer over Na2SO4, filtered off and evaporated totally to give a crude product, which was triturated with ether to give the title compound (750 mg, 53%) as a white solid. MS (ISP) 412.2 [(M+H)+]; mp>250° C.

Workup

  1. extractionextracted twice with EtOAc
  2. customdried
  3. filtrationfiltered off
  4. customevaporated totally
  5. customto give a crude product, which
  6. customwas triturated with ether

Sources & evidence

ORD record
ord-cdee969bb89e44719fd918969cbd2077
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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