Trifluoroacetic acid → HCID 11950267, compound

HRID 2243684Notes

Reaction equation

HRID 2243684 reaction equation
CC([CH2:5][N:6]([CH2:10][CH2:11][NH:12][C:13]1[N:14]=[C:15]([C:32]2[CH:37]=[C:36]([C:38]([NH:40][C:41]3[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=3)=[O:39])[CH:35]=[CH:34][C:33]=2[CH3:48])[C:16]2[CH2:21][NH:20][C:19](=[O:22])[N:18]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=3[F:30])[C:17]=2[N:31]=1)C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:29][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([F:30])[C:23]=1[N:18]1[C:17]2[N:31]=[C:13]([NH:12][CH2:11][CH2:10][NH:6][CH3:5])[N:14]=[C:15]([C:32]3[CH:37]=[C:36]([CH:35]=[CH:34][C:33]=3[CH3:48])[C:38]([NH:40][C:41]3[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=3)=[O:39])[C:16]=2[CH2:21][NH:20][C:19]1=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86608558HCID 86608558, compound

Product 1

HCID 11950267HCID 11950267, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl(2-{[8-(2,6-difluorophenyl)-4-(5-{[(4-fluorophenyl)amino]carbonyl}-2-methylphenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-2-yl]amino}ethyl)methylcarbamate (20 mg, 0.030 mmol) in DCM (5 mL) was added TFA (0.06 mL). The reaction mixture was stirred at room temperature overnight, quenched with triethylamine (0.2 mL) at −78° C. The residue was mixed with H2O (5.0 mL). The organic layer was separated and the aqueous layer was extracted with DCM (3×15 mL). The combined organic phases were washed with saturated aq. NaCl, dried over Na2SO4, filtered, and concentrated. Purification via a CombiFlash system (90% CH2Cl2/7% MeOH/3% NH4OH) then afforded the title compound (11 mg, 65%). LC-MS (ES) m/z 562 (M+H)+; 1H-NMR(MeOD) δ 2.27 (s, 3H), 2.34 (s, 3H), 2.57 (m, 2H), 3.26 (m, 2H), 4.11 (s, 2H), 7.15 (m, 4H), 7.52 (m, 2H), 7.71 (m, 2H), 7.82 (s, 1H), 7.97 (d, 1H).

Workup

  1. customquenched with triethylamine (0.2 mL) at −78° C
  2. additionThe residue was mixed with H2O (5.0 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM (3×15 mL)
  5. washThe combined organic phases were washed with saturated aq. NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification via a CombiFlash system (90% CH2Cl2/7% MeOH/3% NH4OH)

Sources & evidence

ORD record
ord-8c3a201dcef74798abfcdc71ba69f28f
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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