Potassium Carbonate → HCID 21934650, compound

HRID 1241374Notes

Reaction equation

HRID 1241374 reaction equation
[C:1]([C:3]1[S:7][C:6]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([N:15]3[CH2:20][CH2:19][CH2:18][CH:17]([NH:21]C(=O)C(F)(F)F)[CH2:16]3)[CH:10]=2)=[N:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+]>CO.COOOC>[NH2:21][CH:17]1[CH2:18][CH2:19][CH2:20][N:15]([C:11]2[N:12]=[CH:13][N:14]=[C:9]([NH:8][C:6]3[S:7][C:3]([C:1]#[N:2])=[CH:4][N:5]=3)[CH:10]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21934601HCID 21934601, compound

Product 1

HCID 21934650HCID 21934650, compound

Reagents, catalysts & solvents 1

HCID 86585953Methanol dimethoxyetherSolvent

Conditions

Temperature
75 °C

Procedure

Crude N-(1-{6-[(5-cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperidin-3-yl)-2,2,2-trifluoroacetamide 9-5 (0.9 mmol) was suspended/dissolved in methanol/dimethoxyether (5 mL/2 mL) and potassium carbonate (1.8 mmol). This was warmed to 75° C. and stirred overnight. The product was purified on a preparative hplc and isolated via lyophilization from dioxane/water to produce 9-6. Hi-Res MS: calc: 302.1183 found: 302.1190. 1NMR(CD3OD): 8.31 ppm (s, 1H); 7.87 ppm (s, 1H); 6.09 ppm (s, 1H); 4.21 ppm (d, 1H); 4.07 ppm (d, 1H); 3.60 ppm (m, 1H); 2.95 ppm (m, 1H); 2.75 ppm (m, 1H); 2.00 ppm (m, 1H); 1.77 ppm (m, 1H); 1.54 ppm (m, 1H); 1.37 ppm (m, 1H).

Workup

  1. customThe product was purified on a preparative hplc and
  2. customisolated via lyophilization from dioxane/water
  3. customto produce 9-6

Sources & evidence

ORD record
ord-a73adedede7a4d81bdfdd602c8c09c17
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…