Dimethylformamide → HCID 59513774, compound

HRID 1159975Notes

Reaction equation

HRID 1159975 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([C:18](=O)/[CH:19]=[CH:20]/[N:21](C)[CH3:22])=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15](Cl)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N+:25]([O-])(O)=O.[F:29][C:30]1[CH:31]=[C:32]([NH:36]C(N)=O)[CH:33]=[CH:34][CH:35]=1.C([O-])([O-])=O.[K+].[K+].[CH3:46][N:47]([CH:49]=O)C>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([C:18]3[CH:19]=[CH:20][N:21]=[C:22]([NH:36][C:32]4[CH:33]=[CH:34][CH:35]=[C:30]([F:29])[CH:31]=4)[N:25]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([N:47]([CH3:49])[CH3:46])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68644119HCID 68644119, compoundHCID 86618784HCID 86618784, compound

Product 1

HCID 59513774HCID 59513774, compoundYield 42%

Procedure

A mixture of (2E)-1-[2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (500 mg, 1.23 mmol—prepared according to WO 02072581 example 1, p. 77) and N-(3-fluorophenyl)urea nitrate (600 mg, 2.8 mmol) were stirred with K2CO3 (1 g, 6.9 mmol) and DMF (5 mL) at 100° C. for 15 h. The reaction was then stirred at rt for 7 days. The resulting brown solution was concentrated under vacuum, partitioned between EtOAc and water. The organic fraction was washed with brine and dried over MgSO4. The crude solution was concentrated and purified by silica gel column chromatography (20-100% gradient EtOAc/hexanes). The purification yielded 254 mg (42%) of an orange powder. ESIMS (M+H)+=505.13

Workup

  1. concentrationThe resulting brown solution was concentrated under vacuum
  2. custompartitioned between EtOAc and water
  3. washThe organic fraction was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationThe crude solution was concentrated
  6. custompurified by silica gel column chromatography (20-100% gradient EtOAc/hexanes)
  7. customThe purification

Sources & evidence

ORD record
ord-7a80a1fec71648cdb1c5d8ae53eb35a8
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

Loading…