Benzoic Acid → HCID 178522404, compound

HRID 1819462Notes

Reaction equation

HRID 1819462 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](O)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.N=C=N.C1N=CN(C(N2C=NC=C2)=O)C=1.C(N(CC)CC)C>C1COCC1>[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:43])[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[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

7

Reactant 5

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 160435CarbodiimideHCID 178508029HCID 178508029, compound

Product 1

HCID 178522404HCID 178522404, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 THF (1.0 mL). To this solution was added benzoic acid (7.3 mg, 0.06 mmol), Polystyrene-linked Carbodiimide (PS-CDI) (47 mg, 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 reaction was filtered to remove the PS-CDI and the volatiles were removed in vacuo. 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 18 mg (74%) of the target compound, m/z 600.34 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-3d4cb4b07e714bb78d7d7831398c9ef3
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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