Formaldehyde → HCID 118061166, compound

HRID 632764Notes

Reaction equation

HRID 632764 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([C:7]2[C:11]([NH:12][C:13]([C:15]3[N:16]=[C:17]([C:20]4[CH:25]=[CH:24][N:23]=[C:22]([N:26]([CH2:34][C:35]([F:38])([F:37])[F:36])C(=O)OC(C)(C)C)[CH:21]=4)[O:18][CH:19]=3)=[O:14])=[CH:10][N:9]([CH3:39])[N:8]=2)[C:4](=[O:40])[CH2:3]1.[CH2:41]=O.[BH4-].[Na+].CO>C1COCC1>[CH3:39][N:9]1[CH:10]=[C:11]([NH:12][C:13]([C:15]2[N:16]=[C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:34][C:35]([F:36])([F:37])[F:38])[CH:21]=3)[O:18][CH:19]=2)=[O:14])[C:7]([N:5]2[CH2:6][C@@H:2]([NH:1][CH3:41])[CH2:3][C:4]2=[O:40])=[N:8]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 4311764Sodium borohydrideHCID 131735451HCID 131735451, compound

Product 1

HCID 118061166HCID 118061166, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (4-(4-((3-((4S)-4-amino-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)carbamoyl)-1,3-oxazol-2-yl)pyridin-2-yl)(2,2,2-trifluoroethyl)carbamate (83 mg) in THF (0.73 mL) was added 37% formalin (32 μl), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was ice-cooled, sodium borohydride (28 mg) and methanol (0.73 mL) were added thereto, and the mixture was stirred under ice-cooling for 1 hr. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in TFA (0.70 mL), and the solution was stirred at room temperature for 20 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and recrystallized from ethyl acetate/hexane to give the title compound (19 mg).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 1 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in TFA (0.70 mL)
  6. stirringthe solution was stirred at room temperature for 20 min
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  9. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2ba01513086b4d02a062be371ca00e9f
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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