Trifluoroacetic acid → 4-(4-Aminophenylthio)-3-(6-fluoro-7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzoic acid

HRID 605431Notes

Reaction equation

HRID 605431 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[C:34]([F:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[C:34]([F:36])[C:33]([CH:37]([CH3:39])[CH3:38])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670411374-(4-(tert-Butoxycarbonylamino)phenylthio)-3-(6-fluoro-7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzoic acid

Product 1

HCID 670407504-(4-Aminophenylthio)-3-(6-fluoro-7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 451C (0.23 g, 0.4 mmo) in CH2Cl2 (4.6 mL) was treated with trifluoroacetic acid [TFA] (1.15 mL) dropwise at room temperature then stirred for 1 hour. The reaction mixture was concentrated. The residue was diluted with water, made basic with K2CO3, stirred at room temperature overnight. The pH was adjusted to pH 5-6 with 1N HCl stirred at room temperature for 1 hour, the resulting precipitate was collected by filtration, washed with water and i-Pr2O, and dried at 40° C. in vacuum overnight to give the title compound as yellow crystal (0.13 g, 71%). 1H-NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=7.0 Hz, 6H), 3.42-3.60 (m, 1H), 5.64 (br-s, 2H), 6.64 (d, J=8.4 Hz, 2H), 6.84 (d, J=7.7 Hz, 1H), 7.14 (d, J=8.4 Hz, 2H), 7.73 (br-d, J=7.7 Hz, 1H), 7.83 (br-s, 1H), 8.58 (s, 1H), 8.65-8.80 (m, 1H), 10.10 (s, 1H), 12.91 (br-s, 1H). MS ESI+m/z: 450 (M+H), ESI− m/z: 448 (M−H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with water
  3. stirringstirred at room temperature overnight
  4. stirringstirred at room temperature for 1 hour
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water and i-Pr2O
  7. customdried at 40° C. in vacuum overnight

Sources & evidence

ORD record
ord-5c8d471426c44aed93f9d26c7b045e60
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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