Cesium carbonate → HCID 59559853, compound

HRID 1177333Notes

Reaction equation

HRID 1177333 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].[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][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:36][C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][N:38]=3)=[O:20])[CH:9]=2)=[CH:34][C:24]=1[F:23])=[O:27]

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 11528799HCID 11528799, compoundHCID 60637230HCID 60637230, compound

Product 1

HCID 59559853HCID 59559853, 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. 2-Amino-5-methylpyridine (0.214 g, 2 mmol) and HATU (0.67 g, 1.75 mmol) were added. The reaction mixture was stirred at 75° C. for four hours and then filtered. Purification by HPLC gave a solid (92 mg, 17% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.79 (s, 1 H) 8.52 (s, 1 H) 8.21 (m, 1 H) 8.06-8.08 (d, 1 H) 7.68 (m, 1 H) 7.64-7.67 (m, 1 H) 7.37-7.41 (t, 1 H) 7.12 (s, 1 H) 7.02-7.06 (m, 1 H) 6.87-6.90 (m, 1 H) 2.99 (s, 3 H) 2.87 (s, 3 H) 2.59-2.60 (m, 3 H) 2.28 (s, 1 H). LCMS for C25H22FN3O3S m/z 464.10 (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-20faea48cdb847fcb80c352392dbbcbc
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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