Trifluoroacetic acid → HCID 71143541, compound

HRID 571462Notes

Reaction equation

HRID 571462 reaction equation
[C:1]([CH2:3][C:4]1([N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]4[N:31](COCC[Si](C)(C)C)[CH:32]=[CH:33][C:26]=34)[CH:22]=[N:21]2)[CH2:7][N:6]([C:8]2[CH:19]=[CH:18][C:11]([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:10][CH:9]=2)[CH2:5]1)#[N:2].FC(F)(F)C(O)=O>>[C:1]([CH2:3][C:4]1([N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]4[NH:31][CH:32]=[CH:33][C:26]=34)[CH:22]=[N:21]2)[CH2:5][N:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:18][CH:19]=2)[CH2:7]1)#[N:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71143552HCID 71143552, compound

Product 1

HCID 71143541HCID 71143541, compound

Procedure

4-{3-(Cyanomethyl)-3-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]azetidin-1-yl}-N-isopropylbenzamide was dissolved in dichloromethylene (5 mL). To the solution was added trifluoroacetic acid (TFA) (2.5 mL). The mixture was stirred at room temperature for 1 hour. The volatiles were removed under reduced pressure. The residue was dissolved in methanol (10 mL). To the solution was added ethylenediamine (1 mL). The mixture was stirred at room temperature for 4 hours, and was purified by RP-HPLC (pH=10) to afford the desired product (0.415 g). LCMS (M+H)+: m/z=440.1. The high purity (99.6%) of the product was obtained by re-crystallization from acetone-ether. 1H NMR (400 MHz, CDCl3): δ 9.57 (s, 1H), 8.31 (d, J=4.9 Hz, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.70 (m, 2H), 7.39 (d, J=3.4 Hz, 1H), 7.18 (d, J=4.9 Hz, 1H), 6.70 (d, J=3.4 Hz, 1H), 6.55 (m, 2H), 5.79 (d, J=7.8 Hz, 1H), 4.47 (d, J=8.3 Hz, 2H), 4.38 (d, J=8.3 Hz, 2H), 4.27 (m, 1H), 3.45 (s, 2H), 1.25 (d, J=6.7 Hz, 6H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (10 mL)
  3. additionTo the solution was added ethylenediamine (1 mL)
  4. stirringThe mixture was stirred at room temperature for 4 hours
  5. customwas purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-baaca3607499402796a8921cedae7cfd
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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