Ammonium Bicarbonate → HCID 18786356, compound

HRID 1108078Notes

Reaction equation

HRID 1108078 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]([OH:28])=O)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(=O)(O)[O-].[NH4+].C(OC1C=CC2C(=CC=CC=2)[N:38]1C(OCC)=O)C>ClCCl>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]([NH2:38])=[O:28])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 14013Ammonium Bicarbonate2×HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline2×HCID 18786346HCID 18786346, compound

Product 1

HCID 18786356HCID 18786356, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-[3-[4-(pyrrol-1-ylmethyl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylic acid (0.36 g, 0.93 mmol), ammonium bicarbonate (0.44 g, 5.58 mmol) and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.28 g, 1.12 mmol) in dichloromethane (20 ml) were stirred at room temperature overnight. Ammonium bicarbonate and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline were added until the acid was consumed. The reaction mixture was diluted with dichloromethane (50 ml) and washed with water (50 ml). The organic extract was washed with cold 1N hydrochloric acid (50 ml), water (50 ml) and saturated aqueous sodium bicarbonate (5 ml), water (50 ml) and brine (50 ml), dried (magnesium sulfate) and concentrated to dryness. Recrystallization of the residue from ethyl acetate afforded the titled compound (198 mg, 54%).

Workup

  1. customwas consumed
  2. additionThe reaction mixture was diluted with dichloromethane (50 ml)
  3. washwashed with water (50 ml)
  4. extractionThe organic extract
  5. washwas washed with cold 1N hydrochloric acid (50 ml), water (50 ml) and saturated aqueous sodium bicarbonate (5 ml), water (50 ml) and brine (50 ml)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated to dryness
  8. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-790f758284e04288adb9fa29e489ff43
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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