Trifluoroacetic acid → Benzyl 4-{6-[(5-cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}-2-[(isopropylamino) carbonyl]piperazine-1-carboxylate

HRID 1241424Notes

Reaction equation

HRID 1241424 reaction equation
[CH:1]([NH:4][C:5]([CH:7]1[CH2:12][N:11]([C:13](OC(C)(C)C)=O)[CH2:10][CH2:9][N:8]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:6])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.ClC1[N:43]=[CH:42][N:41]=[C:40]([NH:44][C:45]2[S:46][C:47]([C:50]#[N:51])=[CH:48][N:49]=2)[CH:39]=1.C(N(CC)CC)C>>[C:50]([C:47]1[S:46][C:45]([NH:44][C:40]2[N:41]=[CH:42][N:43]=[C:13]([N:11]3[CH2:10][CH2:9][N:8]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])[CH:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:12]3)[CH:39]=2)=[N:49][CH:48]=1)#[N:51]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 116873242-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrileHCID 210599841-Benzyl 4-tert-butyl 2-[(isopropylamino)carbonyl]piperazine-1,4-dicarboxylate

Product 1

HCID 21934713Benzyl 4-{6-[(5-cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}-2-[(isopropylamino) carbonyl]piperazine-1-carboxylate

Conditions

Temperature
150 °C

Procedure

47-2 (0.24 g, 0.78 mmol) was first treated with 3 mL of trifluoroacetic acid for 30 minutes at 25° C. and then the reaction was evaporated to dryness. The residue was dissolved in n-butanol and 35-1 (0.18 g, 0.78 mmol) and triethylamine (0.39 g, 3.88 mmol) were added. After heating at 150° C. for 18 hours, the reaction was cooled and the product was filtered off, washed with n-butanol, ethyl ether and then dried to afford the product 47-3. Hi-Res MS: calc: 507.1921 found: 507.1914. 1H-NMR (DMSO-d6): 12.15(s, 1H); 8.39(s, 1H); 8.25(s, 1H); 7.33(m, 5H); 6.11(s, 1H); 5.14(m, 2H); 4.47(m, 2H); 3.85(m, 2H); 3.69(m, 2H); 3.25(m, 1H); 3.17(m, 1H); 0.93(m, 6H).

Workup

  1. customthe reaction was evaporated to dryness
  2. dissolutionThe residue was dissolved in n-butanol
  3. temperaturethe reaction was cooled
  4. filtrationthe product was filtered off
  5. washwashed with n-butanol, ethyl ether
  6. customdried

Sources & evidence

ORD record
ord-4b6527c3c9874568b8ca84b1f1e825db
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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