Hydrochloric Acid → HCID 69630855, compound

HRID 859111Notes

Reaction equation

HRID 859111 reaction equation
N(OC(C)(C)C)=O.[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[C:15]([NH:19][C:20]2[N:25]=[C:24]([C:26]3[S:30][C:29](N)=[N:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[CH:23]=[CH:22][N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:12])[CH3:9].O.[ClH:37]>C(#N)C.C(Cl)(Cl)Cl>[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[C:15]([NH:19][C:20]2[N:25]=[C:24]([C:26]3[S:30][C:29]([Cl:37])=[N:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[CH:23]=[CH:22][N:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:12])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10906Tert-Butyl nitriteHCID 86595103HCID 86595103, compound

Product 1

HCID 69630855HCID 69630855, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

t-Butyl nitrite (0.87 mL, 6.54 mmol) is added drop-wise to a suspension of N-[3-ethoxycarbonyl-phenyl]-4-(2-amino-4-trifluoromethyl-5-thiazolyl)-2-pyrimidineamine (1.34g, 3.27 mmol) and anhydrous cupric chloride (925 mg, 6.55 mmol) in acetonitrile (15 mL) over 0.5 hours. After stirring at room temperature for 3 hours, water and chloroform are added and the mixture is made acidic with 12N hydrochloric acid. The layers are separated and the aqueous layer is extracted with chloroform. The combined organic extracts are dried over MgSO4, filtered and concentrated. The residue is purified by chromatography on silica gel to give N-[3-ethoxycarbonyl-phenyl]-4-[2-chloro-4-trifluoromethyl-5-thiazolyl]-2-pyrimidineamine (1.1 g); ESI-MS (m/z): 429 (M++H).

Workup

  1. customThe layers are separated
  2. extractionthe aqueous layer is extracted with chloroform
  3. dry with materialThe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d7fa1fc734044b7c945b08695f8cf41c
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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