Hydrochloric Acid → HCID 57520170, compound

HRID 1528101Notes

Reaction equation

HRID 1528101 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=2)=[O:19])[CH2:3][CH2:2]1.[CH2:31]=O.[BH4-].[Na+].Cl>O.CO>[CH3:31][N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:30])[F:28])[N:22]=2)=[O:19])[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 57520094HCID 57520094, compound

Product 1

HCID 57520170HCID 57520170, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 0.12 g of 1-[6-(1,2,3,6-tetrahydro-pyridin-4-yl)-quinolin-4-yl]-3-(6-trifluoromethyl-pyridin-2-yl)-urea (0.290 mmol) were added subsequently 2 ml of methanol, 0.366 ml of formaldehyde (4.64 mmol) and a solution of 0.055 g of sodium borohydride (1.451 mmol) in 0.8 ml of water. The reaction was slightly exotherm. A small amount of 2M HCl was added to the reaction mixture up to a pH of 3 to destroy the excess of sodium bororhydride. After neutralization with sodium bicarbonate, methanol was evaporated under reduced pressure, water added to the residue, the reaction mixture extracted three times with ethylacetate, the organic phases combined and dried over sodium sulfate and the solvent evaporated under reduced pressure. 120 mg of the desired product were obtained as an off white powder (yield: 97%).

Workup

  1. customto destroy the excess of sodium bororhydride
  2. customAfter neutralization with sodium bicarbonate, methanol was evaporated under reduced pressure, water
  3. additionadded to the residue
  4. extractionthe reaction mixture extracted three times with ethylacetate
  5. dry with materialdried over sodium sulfate
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e194a1a72db2400a91363918be88c240
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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