Acetic Acid → HCID 57863424, compound

HRID 1446728Notes

Reaction equation

HRID 1446728 reaction equation
Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]4[CH:26]=[CH:27][C:28]([C:30]5[CH:35]=[CH:34][C:33]([C:36]([N:38]6[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]6)=[O:37])=[CH:32][CH:31]=5)=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:17][C:16]=2[F:44])=[O:13])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH3:45][C:46]([CH3:48])=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]4[CH:26]=[CH:27][C:28]([C:30]5[CH:35]=[CH:34][C:33]([C:36]([N:38]6[CH2:39][CH2:40][N:41]([CH:46]([CH3:48])[CH3:45])[CH2:42][CH2:43]6)=[O:37])=[CH:32][CH:31]=5)=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:17][C:16]=2[F:44])=[O:13])[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 68542631HCID 68542631, compound

Product 1

HCID 57863424HCID 57863424, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1-(5-tert-butyl-isoxazol-3-yl)-3-(2-fluoro-4-{7-[4-(piperazine-1-carbonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-urea hydrochloride (0.290 g, 0.469 mmol) in methanol (5 mL) and acetone (0.041 mL, 0.563 mmol). Add acetic acid (0.032 mL, 0.563 mmol); stir the mixture for five minutes. Add sodium cyanoboro-hydride (0.053 g, 0.845 mmol). Stir the mixture at room temperature for 14 hours. Concentrate to dryness and quench with 1 N HCl (5 mL). Partition between ethyl acetate and 1 N NaOH, wash with aqueous saturated sodium chloride, dry the organics over magnesium sulfate, filter, and concentrate. Purify by column chromatography (hexanes→5% methanol in dichloromethane→10% methanol in dichloromethane→10% 2 M NH3 in methanol in dichloromethane) to afford product (0.019 g, 7%). MS(ES), m/z 624 (M+1).

Workup

  1. stirringStir the mixture at room temperature for 14 hours
  2. concentrationConcentrate to dryness
  3. customquench with 1 N HCl (5 mL)
  4. customPartition between ethyl acetate and 1 N NaOH
  5. washwash with aqueous saturated sodium chloride
  6. dry with materialdry the organics over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by column chromatography (hexanes→5% methanol in dichloromethane→10% methanol in dichloromethane→10% 2 M NH3 in methanol in dichloromethane)

Sources & evidence

ORD record
ord-d467d23e3b3f43df8a1620ca6244b9ff
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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