Benzylamine → HCID 25120534, compound

HRID 1893465Notes

Reaction equation

HRID 1893465 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[C:15]2[N:16]([C:28]([CH:31]=O)=[CH:29][N:30]=2)[C:17]2[C:22]([N:23]=1)=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2.[BH4-].[Na+]>CO>[CH2:1]([NH:8][CH2:31][C:28]1[N:16]2[C:17]3[C:22]([N:23]=[C:14]([NH:13][CH2:12][CH2:11][CH2:10][OH:9])[C:15]2=[N:30][CH:29]=1)=[CH:21][C:20]([C:24]([F:26])([F:27])[F:25])=[CH:19][CH:18]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 4311764Sodium borohydrideHCID 25120537HCID 25120537, compound

Product 1

HCID 25120534HCID 25120534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of the benzylamine (13 μL, 0.12 mmol) in methanol (400 μL) was added 4-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline-1-carbaldehyde (35 mg, 0.10 mmol). The reaction mixture was stirred at 30° C. for 17 h. After addition of NaBH4 (5 mg, 0.12 mmol), the mixture was stirred at 30° C. for 5 h. Then it was concentrated, diluted in ethyl acetate, washed with an aqueous saturated solution of ammonium chloride and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered, concentrated in vacuo to give, after purification by preparative TLC (dichloromethane/methanol 9/1), the title compound (32 mg, 75%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 30° C. for 5 h
  2. concentrationThen it was concentrated
  3. additiondiluted in ethyl acetate
  4. washwashed with an aqueous saturated solution of ammonium chloride
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give
  10. customafter purification by preparative TLC (dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-ac4bf4e628644a6488e8995bfd93ae62
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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