Potassium Carbonate → HCID 11704577, compound

HRID 2102378Notes

Reaction equation

HRID 2102378 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.FC(F)(F)C(O)=O.[NH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([NH:36][CH3:37])=[O:35])=[N:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH3:37][NH:36][C:34]([C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][CH2:24][NH:23][C:2]2[C:3]3[C:10]([C:11]4[S:12][CH:13]=[CH:14][N:15]=4)=[CH:9][S:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:33][N:32]=1)=[O:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57803002HCID 57803002, compoundHCID 68541297HCID 68541297, compound

Product 1

HCID 11704577HCID 11704577, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chloro-5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidine (0.050 g, 0.20 mmol), 5-(3-aminopropoxy)-N-methylpyridine-2-carboxamide trifluoroacetate (0.070 g, 0.22 mmol), potassium carbonate (0.272 g, 1.97 mmol) and N,N-dimethylacetamide (2.4 mL) was heated at 120° C. for 13 h. The solvent was evaporated in vacuo, and the residue was treated with 5% sodium bicarbonate (20 mL) and ethyl acetate (20 mL). The precipitate was filtered and washed with water and ethyl ether. The resulting white solid was purified by column chromatography over silica gel to give 70 mg (81%) N-methyl-5-(3-[5-(1,3-thiazol-2-yl)thieno[2,3-d]pyrimidin-4-yl]aminopropoxy)pyridine-2-carboxamide. MS [M+H]=427, LC/MS (EI) tR 3.54 min (Method D), 1H NMR (10% MeOD/CDCl3) δ (ppm) 10.85 (s, 1H), 8.30 (s, 1H), 8.12 (d, J=2.4 Hz, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.94 (b, 1H), 7.71 (s, 1H), 7.50 (d, J=3.6 Hz, 1H), 7.28 (s, 1H), 7.21 (dd, J=8.7, 3.0 Hz, 1H), 4.15 (t, J=0.6 Hz, 2H), 3.80-3.74 (m, 2H), 2.94 (d, J=0.6 Hz, 3H), 2.24-2.18 (m, 2H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue was treated with 5% sodium bicarbonate (20 mL) and ethyl acetate (20 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with water and ethyl ether
  5. customThe resulting white solid was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-6b55af1badb94a75af36e4922a4b732d
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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