Trifluoroacetic acid → HCID 178476753, compound

HRID 1525346Notes

Reaction equation

HRID 1525346 reaction equation
COC1C=CC(C[O:8][C:9]2[C:14]([C:15]3[O:19][N:18]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([P:26]([CH3:31])(=[O:30])[O:27][CH2:28][CH3:29])=[CH:22][CH:21]=4)[CH:16]=3)=[CH:13][N:12]=[C:11]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[N:10]=2)=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:8][C:9]1[C:14]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[CH:22][C:23]([P:26]([CH3:31])(=[O:30])[O:27][CH2:28][CH3:29])=[CH:24][CH:25]=3)[CH:16]=2)=[CH:13][N:12]=[C:11]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89462877Ethyl 4-(5-(4-(4-methoxybenzyloxy)-2-(pyridin-2-yl)pyrimidin-5-yl)isoxazol-3-yl)phenyl(methyl)phosphinate

Product 1

HCID 178476753HCID 178476753, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 38-f (440 mg, 0.80 mmol) in DCM (5 mL) was added 2,2,2-trifluoroacetic acid (2 mL). After being stir for 10 h at room temperature, the reaction mixture was concentrated under reduce pressure and the residue was purified by pre-TLC (DCM:methanol=15:1) to afford compound 38-g (320 mg, 94%). 1H NMR (300 MHz, CD3OD) δ 8.79-8.80 (m, 1H), 8.71 (s, 1H), 8.38-8.41 (m, 1H), 8.10-8.12 (m, 3H), 7.89-7.93 (m, 2H), 7.67-7.72 (m, 2H), 3.91-3.96 (m, 2H), 1.67-1.72 (d, J=14.4 Hz, 3H), 1.18-1.22 (m, 3H). LC-MS 423 [M+H]+

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by pre-TLC (DCM:methanol=15:1)

Sources & evidence

ORD record
ord-fc59c5e54dd44aed94832dd291e11ede
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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