Hydrochloric Acid → N-(4-(6-(2-Amino-4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

HRID 2055984Notes

Reaction equation

HRID 2055984 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[C:22]([O:24][C:25]2[C:30]3[N:31]=[C:32]([NH:34][C:35](=[O:37])[CH3:36])[S:33][C:29]=3[CH:28]=[CH:27][CH:26]=2)[N:21]=[CH:20][N:19]=1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:11]=[CH:10][C:9]=1[C:18]1[N:19]=[CH:20][N:21]=[C:22]([O:24][C:25]2[C:30]3[N:31]=[C:32]([NH:34][C:35](=[O:37])[CH3:36])[S:33][C:29]=3[CH:28]=[CH:27][CH:26]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11957782tert-Butyl-2-(6-((2-(acetylamino)-1,3-benzothiazol-4-yl)oxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenylcarbamate

Product 1

HCID 21865046N-(4-(6-(2-Amino-4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To {2-[6-(2-acetylamino-benzothiazol-4-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenyl}-carbamic acid tert-butyl ester, (Example 150) (0.35 g, 0.60 mmol) was added 4 M HCl in dioxane (25 mL). The mixture was stirred for 16 h and then was concentrated in vacuum. The residue was dissolved in ethyl acetate (40 mL) and washed with saturated NaHCO3 (2×70 mL), dried over Na2SO4 and concentrated in vacuum. Purification by silica gel chromatography (2:1, EtOAc:hexanes) afforded the title compound as thick yellow oil. Mp: 160-161° C. MS (ESI, pos. ion) m/z: 446 (M+1). Anal. Calcd for C20H14F3N5O2S0.4H2O: C, 53.07; H, 3.30; F, 15.47; N, 12.59. Found: C, 53.12; H, 3.27; F, 15.19; N, 12.70.

Workup

  1. concentrationwas concentrated in vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate (40 mL)
  3. washwashed with saturated NaHCO3 (2×70 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customPurification by silica gel chromatography (2:1, EtOAc:hexanes)

Sources & evidence

ORD record
ord-058c4011156447488e0b3039ecf0afa0
Source dataset
uspto-grants-2008_02
Patent number
US07332511B2

Reaction notes

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