4-Aminobenzoic Acid → HCID 44565644, compound

HRID 406856Notes

Reaction equation

HRID 406856 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]2[CH:11]=[CH:10][CH:9]=[N:8][C:6]=2[N:7]=1.[NH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C.[CH3:37][C:38]1[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[C:39]=1[NH2:40].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(O)CCC>[CH3:37][C:38]1[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[C:39]=1[NH:40][C:23](=[O:25])[C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:2]2[N:3]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]3[CH:11]=[CH:10][CH:9]=[N:8][C:6]=3[N:7]=2)=[CH:27][CH:26]=1

Participants

8

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 68962,6-DimethylanilineHCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57662991HCID 57662991, compound

Product 1

HCID 44565644HCID 44565644, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
138 °C

Procedure

A mixture of 2-chloro-4-phenylpyrido[2,3-d]pyrimidine (233 mg, 0.965 mmol), 4-aminobenzoic acid (133 mg, 0.965 mmol), Hunig's base (300 μL, 1.72 mmol) and n-butanol (5 mL) was heated to 138° C. for 30 min. The solvent was removed on a rotary evaporator to give the intermediate acid as a black oil that was treated with 2,6-dimethylaniline (88 mg, 0.73 mmol), Hunig's base (100 μL, 0.57 mmol) and HATU (137 mg, 0.36 mmol) in DMF (1 mL) The mixture was heated to 60° C. overnight. The reaction was cooled to rt and purified by preparative reverse phase HPLC to give N-(2,6-dimethylphenyl)-4-[(4-phenylpyrido[2,3-d]pyrimidin-2-yl)amino]benzamide (29.6 mg, 18%) as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 8.96 (d, 1H), 8.61-8.58 (m, 1H), 8.20 (d, 2H), 8.05 (d, 2H), 7.86-7.84 (m, 2H), 7.67-7.61 (m, 3H), 7.51 (dd, 1H), 7.13 (s, 3H), 2.27 (s, 6H). MS (EI) for C28H23N5O: 446.0 (MH+).

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. customto give the intermediate acid as a black oil that
  3. temperaturewas heated to 60° C. overnight
  4. temperatureThe reaction was cooled to rt
  5. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-2b08533315b545b1aeb4a7476a6463fd
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

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