Hydrochloric Acid → HCID 22466756, compound

HRID 1935152Notes

Reaction equation

HRID 1935152 reaction equation
CO[CH:3](OC)[CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.Cl.[NH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][C:19]([C:25]#[N:26])=[C:18]2[NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=1.C([BH3-])#N.[Na+]>O.C(O)C.C(O)(=O)C>[Br:34][C:30]1[CH:29]=[C:28]([NH:27][C:18]2[C:17]3[C:22](=[CH:23][CH:24]=[C:15]([NH:14][CH2:3][CH2:4][CH2:5][N:6]4[CH2:10][CH2:9][CH2:8][CH2:7]4)[CH:16]=3)[N:21]=[CH:20][C:19]=2[C:25]#[N:26])[CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 224665861-(3,3-Dimethoxypropyl)pyrrolidine

Product 1

HCID 22466756HCID 22466756, compoundYield 21.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Dissolved 0.64 g (3.69 mmol) 3-(pyrrolidin-1-yl)propionaldehyde dimethyl acetal in 10 ml water and acidified to pH 1 with concentrated HCl. Heated to 40° C. for 90 minutes, removed heat and neutralized with sodium bicarbonate. Dissolved 500 mg (1.47 mmol) 6-amino-4-(3-bromo-phenylamino)-quinoline-3-carbonitrile in 100 ml ethanol and added acetic acid until pH was 3 to 4. Added the deprotected aldehyde to the amine solution and stirred at 25° C. for 0.5 hour. Gradually added 94 mg (1.47 mmol) sodium cyanoborohydride and stirred overnight. Stripped solvent, partitioned between chloroform and water. Washed organic layer with brine and dried with sodium sulfate. Stripped solvent and filtered through a pad of silica gel, first with 10% methanol/chloroform, then 20% methanol/chloroform/1% ammonium hydroxide. Stripped solvent and dried in vacuo, giving 143 mg of yellow-brown solid: mass spectrum (electrospray m/e): M+H=450, 452.1.

Workup

  1. customremoved
  2. temperatureheat
  3. customStripped solvent, partitioned between chloroform and water
  4. dry with materialWashed organic layer with brine and dried with sodium sulfate
  5. filtrationfiltered through a pad of silica gel, first with 10% methanol/chloroform
  6. customdried in vacuo

Sources & evidence

ORD record
ord-435149cc7685490eafc8a6edaf013861
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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