Trifluoroacetic acid → 2-({6-[4-(2-Oxopiperidin-3-yl)piperazin-1-yl]pyrimidin-4-yl}amino)-1,3-thiazole-5-carbonitrile

HRID 1241430Notes

Reaction equation

HRID 1241430 reaction equation
[O:1]=[C:2]1[CH:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][NH:3]1.FC(F)(F)C(O)=O.ClC1[N:34]=[CH:33][N:32]=[C:31]([NH:35][C:36]2[S:37][C:38]([C:41]#[N:42])=[CH:39][N:40]=2)[CH:30]=1.C(N(CC)CC)C>>[O:1]=[C:2]1[CH:7]([N:8]2[CH2:9][CH2:10][N:11]([C:14]3[N:34]=[CH:33][N:32]=[C:31]([NH:35][C:36]4[S:37][C:38]([C:41]#[N:42])=[CH:39][N:40]=4)[CH:30]=3)[CH2:12][CH2:13]2)[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 116873242-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrileHCID 21934693HCID 21934693, compound

Product 1

HCID 101568622-({6-[4-(2-Oxopiperidin-3-yl)piperazin-1-yl]pyrimidin-4-yl}amino)-1,3-thiazole-5-carbonitrile

Conditions

Temperature
150 °C

Procedure

51-2 (0.15 g, 0.53 mmol) was first treated with neat trifluoroacetic acid for 30 minutes at room temperature. The trifluoroacetic acid was then evaporated off and the residue was dissolved in n-butanol (3 mL). To this was added 35-1 (0.13 g, 0.53 mmol) and triethylamine (0.27 g, 2.65 mmol). This was heated at 150° C. for 18 hours and then the solid was filtered off, washed with n-butanol and then ethyl ether to afford 51-3. Hi-Res MS: calc: 385.1554 found: 385.1551. 1H-NMR (DMSO-d6): 12.02 (s, 1H); 8.41 (s, 1H); 8.25 (s, 1H); 7.44 (s, 1H); 6.20 (s, 1H); 3.51 (br s, 4H); 3.13 (m, 1H); 3.05 (m, 2H); 2.93 (m, 2H); 2.63 (m, 2H); 1.62–1.83 (complex, 4H).

Workup

  1. customThe trifluoroacetic acid was then evaporated off
  2. dissolutionthe residue was dissolved in n-butanol (3 mL)
  3. filtrationthe solid was filtered off
  4. washwashed with n-butanol
  5. customethyl ether to afford 51-3

Sources & evidence

ORD record
ord-185af04a38b144d492e96dcef4dfffbc
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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