Benzoic Acid → HCID 18186449, compound

HRID 1357527Notes

Reaction equation

HRID 1357527 reaction equation
[NH2:1][C:2]1[C:3]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]([OH:22])[CH2:18][N:19]([CH3:21])[CH3:20])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C:30](O)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[NH:23]([C:3]1[C:2]([NH:1][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:7][N:6]=[C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]([OH:22])[CH2:18][N:19]([CH3:21])[CH3:20])=[CH:11][CH:10]=2)[N:4]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 18186474HCID 18186474, compound

Product 1

HCID 18186449HCID 18186449, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-4-anilino-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine (Example 108; 100 mg, 0.25 mmol) and benzoic acid (30 mg, 0.25 mmol) were dissolved in DMF (3 ml). 4-N,N-dimethylaminopyridine (90 mg, 0.74 mmol) and 1-(3-N,N-dimethylaminopropyl-3-ethylcarbodiimide) hydrochloride (72 mg, 0.38 mmol) were added and the solution was stirred overnight. Silica (1 g) was added and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 0-10% 2M methanolic ammonia in DCM. Concentration of the appropriate fractions gave the product as a solid (25 mg, 20%). NMR: 2.2 (s, 6H), 2.4 (m, 2H), 3.9 (m, 3H), 6.8 (d, 2H), 7.0 (t, 1H), 7.3 (t, 2H), 7.55 (m, 5H), 7.65 (d, 2H), 7.95 (s, 1H), 8.05 (d, 2H), 8.6 (s, 1H), 9.0 (s, 1H), 8.6 (s, 1H); MS (MH+): 499.

Workup

  1. additionSilica (1 g) was added
  2. customvolatile material was removed by evaporation
  3. customThe residue was purified by column chromatography
  4. washeluting with 0-10% 2M methanolic ammonia in DCM

Sources & evidence

ORD record
ord-227fd79e8de14ea9b96bddcd0a600271
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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