Trifluoroacetic acid → HCID 58292933, compound

HRID 1948064Notes

Reaction equation

HRID 1948064 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:35]4[CH2:36][CH2:37][N:38](C(OC(C)(C)C)=O)[CH2:39][CH:40]=4)=[C:28]4[C:32]=3[C:31](=[O:33])[N:30]([CH3:34])[CH2:29]4)[C:20]([C:48]([F:51])([F:50])[F:49])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:7]([O:6][P:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:35]4[CH2:36][CH2:37][NH:38][CH2:39][CH:40]=4)=[C:28]4[C:32]=3[C:31](=[O:33])[N:30]([CH3:34])[CH2:29]4)[C:20]([C:48]([F:50])([F:51])[F:49])=[CH:19][N:18]=2)=[CH:14][CH:15]=1)(=[O:5])[O:3][CH2:1][CH3:2])[CH3:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86654047HCID 86654047, compound2×

Product 1

HCID 58292933HCID 58292933, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(7-{[2-({4-[(diethoxyphosphoryl)methyl]phenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate (Compound 246A, 180 mg, 0.25 mmol) was added methylene chloride (1 mL) and trifluoroacetic acid (1 mL). The mixture was stirred at room temperature for 1 hour, after which, the reaction mixture was concentrated and purified by MDP. 1H NMR (400 MHz, methanol-d4) δ=1.27 (t, J=6.9 Hz, 6H), 2.77-2.85 (m, 2H), 3.19 (s, 3H), 3.29 (d, J=21.5 Hz, 2H), 3.50 (t, J=6.1 Hz, 2H), 3.88-3.94 (m, 2H), 4.01-4.17 (m, 4H), 4.59 (s, 2H), 6.02 (dt, J=3.3, 1.7 Hz, 1H), 7.35 (dd, J=8.5, 2.4 Hz, 2H), 7.50 (d, J=8.8 Hz, 1H), 7.57 (d, J=8.1 Hz, 2H), 8.35-8.43 (m, 1H), 8.72 (br. s., 1H). MS (ES+): m/z 631.23 (100) [MH+]; HPLC: tR=0.68 min (UPLC, purity).

Workup

  1. concentrationafter which, the reaction mixture was concentrated
  2. custompurified by MDP

Sources & evidence

ORD record
ord-c73b4ab15b8d4ed7a707b309b652891f
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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