Cesium carbonate → HCID 66756360, compound

HRID 1177336Notes

Reaction equation

HRID 1177336 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[C:13]2[S:14][CH:15]=[CH:16][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.CN(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:13]3[S:14][CH:15]=[CH:16][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 11310602ethyl 7-hydroxybenzo[b]thiophene-5-carboxylate

Product 1

HCID 66756360HCID 66756360, 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 7-hydroxybenzo[b]thiophene-5-carboxylate (0.275 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 (0.21 g, 2.17 mmol) and then HATU (0.71 g, 1.87 mmol) were added. The reaction mixture was stirred at 50° C. for one hour and then filtered. Purification by HPLC gave a solid (6 mg, 1% yield) as expected product. 1H NMR (400 MHz, CD3OD) δ 8.38 (s, 1 H) 7.96-7.99 (m, 2 H) 7.73-7.76 (m, 1 H) 7.58-7.61 (m, 2 H) 7.53 (s, 1 H) 7.23-7.28 (m, 2 H) 6.60 (s, 1 H) 3.84 (s, 3 H) 3.13 (s, 3 H). LCMS for C20H17N3O4S2 m/z 428.10 (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-223c86bbb5ed419e9dfabb7e13dbb7ef
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…