Diisopropylethylamine → HCID 54204450, compound

HRID 612026Notes

Reaction equation

HRID 612026 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1.C(N(C(C)C)CC)(C)C.[CH3:31][O:32][CH2:33]/[CH:34]=[CH:35]/[C:36](Cl)=[O:37].C(=O)(O)[O-].[Na+]>>[Br:21][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:36](=[O:37])[CH:35]=[CH:34][CH2:33][O:32][CH3:31])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 224665544-Methoxycrotonyl chloride

Product 1

HCID 54204450HCID 54204450, compound

Procedure

To a solution of 1.0 g (2.95 mmol) of of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile and 0.57 g (4.42 mmol) of diisopropylethyl amine at 0° C. with stirring was added 0.43 g (3.24 mmol) of 4-methoxycrotonyl chloride. After 1.5 hr at 0° C., the mixture was poured into a saturated solution of sodium bicarbonate and then extracted with ethyl acetate. The organic solution was dried over magnesium sulfate and the sovent was removed. The residue was recrystallized from 1-butanol giving 1.3 g of 4-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-3-cyano-quinolin-6-yl]-amide as a yellow solid: mass spectrum (electrospray, m/e,): M+H 436.4, 438.9.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customthe sovent was removed
  4. customThe residue was recrystallized from 1-butanol giving 1.3 g of 4-Methoxy-but-2-enoic acid [4-(3-bromo-phenylamino)-3-cyano-quinolin-6-yl]-amide as a yellow solid

Sources & evidence

ORD record
ord-002917d067264a548c728018a48e40d4
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

Loading…