Cesium carbonate → HCID 66755939, compound

HRID 1177332Notes

Reaction equation

HRID 1177332 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[C:16]2[CH:15]=[CH:14][S:13][C:12]=2[CH:11]=[C:10]([C:17]([O:19]CC)=O)[CH:9]=1.F[C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.[CH3:33][N:34]1[CH:38]=[CH:37][C:36]([NH2:39])=[N:35]1.[CH3:40]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:32][S:29]([C:26]1[CH:27]=[CH:28][C:23]([O:7][C:8]2[C:16]3[CH:15]=[C:14]([CH3:40])[S:13][C:12]=3[CH:11]=[C:10]([C:17]([NH:39][C:36]3[CH:37]=[CH:38][N:34]([CH3:33])[N:35]=3)=[O:19])[CH:9]=2)=[CH:24][CH:25]=1)(=[O:31])=[O:30]

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 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 11379055ethyl 4-hydroxy-1-benzothiophene-6-carboxylate

Product 1

HCID 66755939HCID 66755939, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxybenzo[b]thiophene-6-carboxylate (0.293 g, 1.24 mmol) and 1-fluoro-4-(methylsulfonyl)benzene (0.22 g, 1.26 mmol) in DMF (5 mL). The mixture was stirred at 120° C. for 8 hours and then cooled to room temperature. 1-Methyl-1H-pyrazol-3-amine (0.18 g, 1.85 mmol) and HATU (0.7 g, 1.85 mmol) were added. The reaction mixture was stirred at 50° C. for one hour and then filtered. Purification by HPLC gave a solid (107 mg, 20% yield) as expected product. 1 H NMR (400 MHz, DMSO-d6) δ 10.91 (s, 1 H) 8.51 (s, 1 H) 7.92-7.94 (m, 2 H) 7.71 (m, 1 H) 7.60-7.61 (m, 1 H) 7.20-7.23 (m, 2 H) 7.08-7.10 (m, 1 H) 6.58-6.59 (m, 1 H) 3.78 (s, 3 H), 3.21 (s, 3H), 2.58 (m, 3 H). LCMS for C21H19N3O4S2 m/z 442.10 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. stirringThe reaction mixture was stirred at 50° C. for one hour
  3. filtrationfiltered
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-3e1f3a5ff3484a389862dcf60b532881
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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