Cesium carbonate → HCID 118523035, compound

HRID 529850Notes

Reaction equation

HRID 529850 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH:26]([F:28])[F:27])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][NH:10][N:9]=2)[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].CS(O[CH2:40][CH:41]=[C:42]1[CH2:51][CH2:50][C:45]2([O:49][CH2:48][CH2:47][O:46]2)[CH2:44][CH2:43]1)(=O)=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH:26]([F:28])[F:27])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH2:40][CH:41]=[C:42]3[CH2:51][CH2:50][C:45]4([O:46][CH2:47][CH2:48][O:49]4)[CH2:44][CH2:43]3)[N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 118522897HCID 118522897, compoundHCID 178522413HCID 178522413, compound

Product 1

HCID 118523035HCID 118523035, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (1.50 g, 3.71 mmol) in N,N-dimethylformamide (120 mL) was added Cs2CO3 (3.62 g, 11.11 mmol) and 2-[1,4-dioxaspiro[4.5]decan-8-ylidene]ethyl methanesulfonate (1.94 g, 7.39 mmol) at room temperature. The resulting solution was stirred for 4 h at room temperature and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/petroleum ether (3/2) to give 1.59 g (75%) of N-[3-[5-chloro-2-(difluoromethoxy)phenyl]-1-(2-[1,4-dioxaspiro[4.5]decan-8-ylidene]ethyl)-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide as a light yellow solid. LCMS (Method 31) [M+H]+=571.4, RT=1.21 min.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/petroleum ether (3/2)

Sources & evidence

ORD record
ord-d3ad8d16abb74f11a4637341ffacdf0d
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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