Acetic Anhydride → HCID 178474364, compound

HRID 1819461Notes

Reaction equation

HRID 1819461 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C@H:6]2[CH2:11][CH2:10][C@H:9]([CH2:12][NH:13][C:14]3[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]([NH:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[O:31][C:32]([F:35])([F:34])[F:33])[N:15]=3)[CH2:8][CH2:7]2)[CH2:3]1.[C:36](OC(=O)C)(=[O:38])[CH3:37].C(N(CC)CC)C>C(Cl)Cl>[N+:20]([C:19]1[C:14]([NH:13][CH2:12][C@H:9]2[CH2:10][CH2:11][C@H:6]([N:4]3[CH2:5][CH:2]([NH:1][C:36](=[O:38])[CH3:37])[CH2:3]3)[CH2:7][CH2:8]2)=[N:15][C:16]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][C:32]([F:34])([F:35])[F:33])=[N:17][CH:18]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178508029HCID 178508029, compound

Product 1

HCID 178474364HCID 178474364, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

N4-{[Trans-4-(3-aminoazetidin-1-yl)cyclohexyl]methyl}-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (20 mg, 0.04 mmol) was dissolved in CH2Cl2 (1.0 mL). To this solution was added acetic anhydride (0.057 mL, 0.06 mmol) followed by triethylamine (0.084 mL, 0.06 mmol). The reaction was allowed to stir at 25° C. for 18 h. The volatiles were removed and the crude was redissolved in CH2Cl2 and extracted with 10% aqueous NaHCO3. The aqueous phase was separated and extracted two more times with CH2Cl2. The organic layers were combined, dried (Na2SO4), decanted and concentrated. The resultant residue was purified via flash chromatography (SiO2, 10-30% (2:18:80, NH4OH:CH3OH:CH2Cl2)—CH2Cl2) to afford 16 mg (74%) of the target compound, m/z 538.46 (M+1)+.

Workup

  1. customThe volatiles were removed
  2. dissolutionthe crude was redissolved in CH2Cl2
  3. extractionextracted with 10% aqueous NaHCO3
  4. customThe aqueous phase was separated
  5. extractionextracted two more times with CH2Cl2
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. concentrationconcentrated
  9. customThe resultant residue was purified via flash chromatography (SiO2, 10-30% (2:18:80, NH4OH:CH3OH:CH2Cl2)—CH2Cl2)

Sources & evidence

ORD record
ord-dac41ca27b184759bbd9e17d04ffc2e8
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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