Acetic Acid → HCID 11755037, compound

HRID 747120Notes

Reaction equation

HRID 747120 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]2[CH:27]=[CH:26][C:22]3[N:23]=[CH:24][S:25][C:21]=3[CH:20]=2)[CH:13]=1.C(O)(=O)C.[CH:32]1([CH:38]=O)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOC(C)=O.ClCCCl>[S:25]1[C:21]2[CH:20]=[C:19]([NH:18][C:14]3[CH:13]=[C:12]([C:3]4[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=4[NH:1][CH2:38][CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[N:17]=[CH:16][N:15]=3)[CH:27]=[CH:26][C:22]=2[N:23]=[CH:24]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10068785HCID 10068785, compound

Product 1

HCID 11755037HCID 11755037, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a 5-mL, round-bottomed flask was added [6-(2-amino-4-trifluoromethylphenyl)pyrimidin-4-yl]benzothiazol-6-ylamine (0.060 g, 0.15 mmol), 1,2-dichloroethane (1 mL), acetic acid (0.018 mL, 0.31 mmol) and cyclohexanecarboxaldehyde (0.055 mL, 0.45 mmol, Aldrich). Sodium triacetoxy-borohydride (0.083 g, 0.39 mmol, Aldrich) was added to the mixture with stirring at 0° C. and the mixture was stirring for 17 h at room temperature. The reaction mixture was diluted with EtOAc (3 mL) and quenched with H2O (3 mL) and satd NaHCO3 (7 mL). The phases were separated and the aqueous phase was extracted with EtOAc (3×3 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo onto silica gel. Purification by silica gel chromatography with gradient from 20% to 50% solution of EtOAc in hexane afforded the title compound as a yellow solid. MS (ESI, pos. ion.) m/z: 484 (M+1).

Workup

  1. stirringthe mixture was stirring for 17 h at room temperature
  2. customquenched with H2O (3 mL) and satd NaHCO3 (7 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc (3×3 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo onto silica gel
  8. customPurification by silica gel chromatography with gradient from 20% to 50% solution of EtOAc in hexane

Sources & evidence

ORD record
ord-77e0bdc3b0e04079bb45fe148f893a65
Source dataset
uspto-grants-2008_07
Patent number
US07396831B2

Reaction notes

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