Sodium Bicarbonate → HCID 11684057, compound

HRID 548461Notes

Reaction equation

HRID 548461 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.Cl.[CH3:23][N:24]1[CH2:31][CH2:30][CH:29]=[C:26]([CH2:27]Cl)[CH2:25]1.C(=O)(O)[O-:33].[Na+]>O1CCCC1>[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:27]([C:26]4[CH2:25][N:24]([CH3:23])[CH2:31][CH2:30][CH:29]=4)=[O:33])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 14615850HCID 14615850, compound

Product 1

HCID 11684057HCID 11684057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1 g (2.95 mmol) of 6-amino-4-[(3-bromophenyl)amino]-quinoline-3-carbonitrile and 1.9 g (14.7 mmol) of dissopropylethylamine was strirred in 19 ml of tetrahydrofuran and solid N-methyl-1,2,5,6-tetrahydronicotinyl chloride hydrochloride was added portionwise at 0° C. After stirring 1 hr at 0° C. and 2 hr at room temperature, the mixture was poured into saturated sodium bicarbonate and extracted with ethylacetate. The solution was dried over magnesium sulfate. Sovent was removed and the residue was recrystalized from methanol-ethylacetate giving 0.92 g of a yellow powder: mass spectrum (electrospray, m/e,): M+H 462.4, 464.4.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialThe solution was dried over magnesium sulfate
  3. customSovent was removed
  4. customthe residue was recrystalized from methanol-ethylacetate giving 0.92 g of a yellow powder

Sources & evidence

ORD record
ord-87fc3d965d0540caad23f458883c3914
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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