Cesium carbonate → HCID 59560273, compound

HRID 1177334Notes

Reaction equation

HRID 1177334 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[C:16]2[CH:15]=[C:14]([CH3:17])[S:13][C:12]=2[CH:11]=[C:10]([C:18]([O:20]CC)=O)[CH:9]=1.[F:23][C:24]1[CH:34]=[C:33](F)[CH:32]=[CH:31][C:25]=1[C:26]([N:28]([CH3:30])[CH3:29])=[O:27].[CH3:36][N:37]1[CH:41]=[CH:40][C:39]([NH2:42])=[N:38]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:29][N:28]([CH3:30])[C:26]([C:25]1[CH:31]=[CH:32][C:33]([O:7][C:8]2[C:16]3[CH:15]=[C:14]([CH3:17])[S:13][C:12]=3[CH:11]=[C:10]([C:18]([NH:42][C:39]3[CH:40]=[CH:41][N:37]([CH3:36])[N:38]=3)=[O:20])[CH:9]=2)=[CH:34][C:24]=1[F:23])=[O:27]

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 1372541-Methyl-3-aminopyrazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11528799HCID 11528799, compoundHCID 60637230HCID 60637230, compound

Product 1

HCID 59560273HCID 59560273, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxy-2-methylbenzo[b]thiophene-6-carboxylate (0.275 g, 1.16 mmol) and 2,4-difluoro-N,N-dimethylbenzamide (0.269 g, 1.45 mmol) in DMF (5 mL). The mixture was stirred at 150° C. for 8 hours and then cooled to room temperature. 1-Methyl-1H-pyrazol-3-amine (0.19 g, 1.98 mmol) and HATU (0.664 g, 1.75 mmol) were added. The reaction mixture was stirred at 80° C. for one hour and then filtered. Purification by HPLC gave a solid (100 mg, 19% yield) as expected product. 1H NMR (400 MHz, CD3OD) δ 8.27 (s, 1 H) 7.54 (m, 1 H) 7.48 (m, 1 H) 7.34-7.38 (t, 1 H) 7.00 (s, 1 H) 6.82-6.89 (m, 2 H) 6.59-6.60 (m, 1 H) 3.81 (s, 3 H) 3.09 (s, 3 H) 2.97 (m, 3 H) 2.58 (m, 3 H). LCMS for C23H21FN4O3S m/z 453.10 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. stirringThe reaction mixture was stirred at 80° C. for one hour
  3. filtrationfiltered
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-792c74811bb443d18003281bfafa3c5a
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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