HCID 131730982, compound → HCID 131730981, compound

HRID 2035516Notes

Reaction equation

HRID 2035516 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([F:33])[CH:32]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH:24]=[CH2:25])(=[O:23])=[O:22])=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[CH2:26][C:27]([NH2:29])=[O:28]>CO.C(NCC)C>[CH2:5]([N:6]([CH2:7][CH3:8])[CH2:25][CH2:24][S:21]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:11]2[N:10]=[CH:9][C:8]([CH2:26][C:27]([NH2:29])=[O:28])=[C:7]([NH:6][CH2:5][C:4]3[CH:30]=[C:31]([F:33])[CH:32]=[C:2]([F:1])[CH:3]=3)[CH:12]=2)=[CH:19][CH:18]=1)(=[O:23])=[O:22])[CH3:4]

Participants

4

Reactant 1

HCID 131730982HCID 131730982, compound2×

Product 1

HCID 131730981HCID 131730981, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8021DiethylamineSolvent

Procedure

89 mg of 4-[(3,5-difluorobenzyl)amino]-6-({4-[(vinylsulfonyl)amino]phenyl}amino)pyridine-3-carboxyamide (the compound of Example 303) was dissolved in 1 mL of methanol, to which 0.28 mL of diethylamine was added, and stirred using a microwave reaction apparatus in an argon atmosphere at 120° C. for 30 minutes. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:ammonia methanol=10:1), and solidified in acetone-ether to obtain 41 mg (yield 29%: 2 steps) of the title compound as a white powder.

Workup

  1. additionwas added
  2. customa microwave reaction apparatus in an argon atmosphere at 120° C. for 30 minutes
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-7a99a01b09004ef2b9711301d1d0d2fa
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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