Cesium carbonate → HCID 59559881, compound

HRID 1177327Notes

Reaction equation

HRID 1177327 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].[NH2:35][C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][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:35][C:36]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][N:37]=3)=[O:19])[CH:9]=2)=[CH:33][C:23]=1[F:22])=[O:26]

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 153482-Amino-5-methylpyridineHCID 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 59559881HCID 59559881, 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 (0.286 g, 1.55 mmol) in DMF (5 mL). The mixture was stirred at 150° C. for 8 hours and then cooled to room temperature. 2-Amino-5-methyl pyridine (0.228 g, 2.11 mmol) and then HATU (0.7 g, 1.85 mmol) were added. The reaction mixture was stirred at 75° C. for four hours and then filtered. Purification by HPLC gave a solid (57 mg, 10% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.84 (s, 1 H) 8.64 (s, 1 H) 8.22 (m, 1 H) 8.07-8.09 (d, 1 H)) 8.01-8.02 (d, 1 H) 7.69 (m, 1 H) 7.65-7.68 (m, 1 H) 7.39-7.43 (m, 2 H) 7.08-7.11 (m, 1 H) 6.93-6.95 (m, 1 H) 2.99 (s, 3 H) 2.87 (m, 3 H) 2.28 (s, 3 H). LCMS for C24H20FN3O3S m/z 450.10 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. stirringThe reaction mixture was stirred at 75° C. for four hours
  3. filtrationfiltered
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-98a76eb958214396b8aa6b82ff4bb1ab
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…