Acetic Acid → HCID 86700241, compound

HRID 879434Notes

Reaction equation

HRID 879434 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:41][C:42]([CH3:44])=O.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:32]([CH3:33])=[CH:31][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:26][CH2:27][N:28]([CH:42]([CH3:44])[CH3:41])[CH2:29][CH2:30]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 86700238HCID 86700238, compound

Product 1

HCID 86700241HCID 86700241, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(piperazin-1-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (0.144 mmol) in ethanol (2.0 mL) was added acetone (0.21 mL) and acetic acid (12 μL, 0.21 mmol) at 0° C. Reaction mixture was stirred for 15 minutes, then sodium cyanoborohydride (10 mg, 0.158 mmol) was added and reaction mixture was warmed to room temperature over 2 h. Reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate/brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 10% MeOH/CH2Cl2) to give product. LCMS-ESI+: calc'd for C34H42ClN4O3S: 622.2 (M+H+); Found: 621.3 (M+H+).

Workup

  1. customReaction mixture
  2. customreaction mixture
  3. customReaction mixture
  4. washwashed with saturated sodium bicarbonate/brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CombiFlash (0 to 10% MeOH/CH2Cl2)
  9. customto give product

Sources & evidence

ORD record
ord-2b24c7fb0c004d63b15aad6a8fb3b5e5
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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