Trifluoroacetic acid → Sodium 2-(3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-(methoxycarbonylamino)phenylthio)benzamido)-2-methylpropyl phosphate

HRID 605404Notes

Reaction equation

HRID 605404 reaction equation
C([O:5][P:6]([O:13][CH2:14][C:15]([NH:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([S:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:38])[O:36][CH3:37])=[CH:30][CH:29]=2)=[C:23]([NH:39][C:40]2[C:41]3[CH:49]=[CH:48][C:47]([CH:50]([CH3:52])[CH3:51])=[N:46][C:42]=3[N:43]=[CH:44][N:45]=2)[CH:22]=1)=[O:20])([CH3:17])[CH3:16])([O:8]C(C)(C)C)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+:64]>C(Cl)Cl>[P:6]([O-:7])([O-:8])([O:13][CH2:14][C:15]([NH:18][C:19](=[O:20])[C:21]1[CH:26]=[CH:25][C:24]([S:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([O:36][CH3:37])=[O:38])=[CH:30][CH:29]=2)=[C:23]([NH:39][C:40]2[C:41]3[CH:49]=[CH:48][C:47]([CH:50]([CH3:51])[CH3:52])=[N:46][C:42]=3[N:43]=[CH:44][N:45]=2)[CH:22]=1)([CH3:17])[CH3:16])=[O:5].[Na+:64].[Na+:64]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67040540HCID 67040540, compound

Product 1

HCID 67040987Sodium 2-(3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-(methoxycarbonylamino)phenylthio)benzamido)-2-methylpropyl phosphateYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 441E (240 mg., 0.32 mmol) in CH2Cl2 (1.6 ml.) was reacted with TFA (1.6 ml.) at room temperature for 30 min. The reaction was concentrated, redissolved in water (4 mL) and treated with solid NaHCO3 (270 mg., 3.2 mmol) with stirring. The solution was purified on a C-18 column eluted with a gradient of methanol in water (0-100%). to give the title compound (202 mg., 92%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.17-1.40 (m, 12 H) 2.98-3.11 (m, 1 H) 3.66 (s, 3 H) 6.65 (s, 1 H) 7.18-7.27 (m, 1 H) 7.32 (d, J=8.09 Hz, 2 H) 7.48 (d, J=8.09 Hz, 2 H) 7.51-7.62 (m, 1 H) 7.94 (s, 1 H) 8.18-8.29 (s, 1 H) 8.77 (s, 1 H) 9.84 (s, 1 H)

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in water (4 mL)
  3. customThe solution was purified on a C-18 column
  4. washeluted with a gradient of methanol in water (0-100%)

Sources & evidence

ORD record
ord-0dfc92e09a1a4669847211a0dc4e9225
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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