Cesium carbonate → HCID 59560107, compound

HRID 1177326Notes

Reaction equation

HRID 1177326 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:22][C:23]1[CH:33]=[C:32](F)[CH:31]=[CH:30][C:24]=1[C:25]([N:27]([CH3:29])[CH3:28])=[O:26].[CH3:35][N:36]1[CH:40]=[CH:39][C:38]([NH2:41])=[N:37]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:28][N:27]([CH3:29])[C:25]([C:24]1[CH:30]=[CH:31][C:32]([O:7][C:8]2[C:16]3[CH:15]=[CH:14][S:13][C:12]=3[CH:11]=[C:10]([C:17]([NH:41][C:38]3[CH:39]=[CH:40][N:36]([CH3:35])[N:37]=3)=[O:19])[CH:9]=2)=[CH:33][C:23]=1[F:22])=[O:26]

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 11379055ethyl 4-hydroxy-1-benzothiophene-6-carboxylateHCID 60637230HCID 60637230, compound

Product 1

HCID 59560107HCID 59560107, 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-hydroxybenzo[b]thiophene-6-carboxylate (0.275 g, 1.24 mmol) and 2,4-difluoro-N,N-dimethylbenzamide (0.234 g, 1.26 mmol) in DMF (5 mL). The mixture was stirred at 150° C. for 10 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 (200 mg, 38% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.96 (s, 1 H) 8.59 (m, 1 H) 8.00 (m, 1 H)) 7.61-7.68 (m, 2 H) 7.39-7.43 (m, 2 H) 7.08-7.11 (m, 1 H) 6.92-6.95 (m, 1 H) 6.60 (s, 1 H) 3.79 (s, 3 H) 3.00 (s, 3 H) 2.88 (m, 3 H). LCMS for C22 H19FN4O3S m/z 439.10 (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-5309fc0118bd48839d2957a371d3379c
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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