Trifluoroacetic acid → 2-(1-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperidin-4-yl)-N-isopropylacetamide

HRID 1241422Notes

Reaction equation

HRID 1241422 reaction equation
[CH:1]([NH:4][C:5](=[O:20])[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13](OC(C)(C)C)=O)[CH2:9][CH2:8]1)([CH3:3])[CH3:2].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>C(O)CCC>[C:41]([C:38]1[S:37][C:36]([NH:35][C:31]2[N:32]=[CH:33][N:34]=[C:13]([N:10]3[CH2:9][CH2:8][CH:7]([CH2:6][C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[O:20])[CH2:12][CH2:11]3)[CH:30]=2)=[N:40][CH:39]=1)#[N:42]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 116873242-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrileHCID 21934696Tert-butyl 4-[2-(isopropylamino)-2-oxoethyl]piperidine-1-carboxylate

Product 1

HCID 101106372-(1-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperidin-4-yl)-N-isopropylacetamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

46-2 (0.21 g, 0.73 mmol) was treated with neat trifluoroacetic acid for 20 minutes and then the trifluoroacetic acid was evaporated off. This residue and 35-1 (0.17 g, 0.73 mmol) and triethylamine (0.37 g, 3.67 mmol) were heated at 150° C. for 3 hours in n-butanol. Upon cooling the precipitate was filtered off, washed with n-butanol and ethyl ether and then dried to afford 46-3. Hi-Res MS: calc: 386.1758 found: 386.1754. 1H-NMR (CD3OD): 8.36(s, 1H); 7.99(s, 1H); 6.14(s, 1H); 4.40(d, 2H); 3.98(m, 1H); 2.94(t, 2H); 2.10(complex, 3H); 1.77(d, 2H); 1.22(m, 2H); 1.13(d, 6H).

Workup

  1. customthe trifluoroacetic acid was evaporated off
  2. temperatureUpon cooling the precipitate
  3. filtrationwas filtered off
  4. washwashed with n-butanol and ethyl ether
  5. customdried
  6. customto afford 46-3

Sources & evidence

ORD record
ord-5ef440511e1247728e37bb969186f171
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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