HCID 67513042, compound → HCID 67514126, compound

HRID 339713Notes

Reaction equation

HRID 339713 reaction equation
Cl[C:2]1[C:3]([NH:12][S:13]([C:16]2[CH:20]=[CH:19][N:18]([C:21]([F:28])([F:27])[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[N:17]=2)(=[O:15])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:29][C:30]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[C:38]([O:44][CH3:45])[C:31]=1[O:32][CH2:33][CH2:34][CH:35]([OH:37])[CH3:36]>C(O)CC>[F:27][C:21]([F:28])([N:18]1[CH:19]=[CH:20][C:16]([S:13](=[O:15])(=[O:14])[NH:12][C:3]2[C:2]([NH:29][C:30]3[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[C:38]([O:44][CH3:45])[C:31]=3[O:32][CH2:33][CH2:34][CH:35]([OH:37])[CH3:36])=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[N:17]1)[C:22]([N:24]([CH3:26])[CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 67513042HCID 67513042, compoundHCID 86692800HCID 86692800, compound

Product 1

HCID 67514126HCID 67514126, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

300 mg of 2-[3-(3-chloroquinoxalin-2-ylsulfamoyl)pyrazol-1-yl]-2,2-difluoro-N,N-dimethylacetamide and 258 mg of 4-(2-amino-4,6-dimethoxyphenoxy)butan-2-ol in 4 ml of 1-propanol are heated at 140° C. in a microwave-suitable glass vessel with high absorption in the microwave until starting material 1 has reacted virtually completely (about 45 minutes). The cooled reaction mixture is filtered off with suction, rinsed with 1-propanol and dried, giving 320 mg of 2,2-difluoro-2-(3-{3-[2-(3-hydroxybutoxy)-3,5-dimethoxyphenylamino]quinoxalin-2-ylsulfamoyl}pyrazol-1-yl)-N,N-dimethylacetamide as slightly yellowish solid (yield 74%). MS-FAB (M+H+)=636.2. Rf (polar method): 2.41 min.

Workup

  1. customhas reacted virtually completely (about 45 minutes)
  2. customThe cooled reaction mixture
  3. filtrationis filtered off with suction
  4. washrinsed with 1-propanol
  5. customdried

Sources & evidence

ORD record
ord-9919d00668b1439f843f6f5f0b56455f
Source dataset
uspto-grants-2014_11
Patent number
US08895559B2

Reaction notes

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