Ammonia → HCID 69338674, compound

HRID 722192Notes

Reaction equation

HRID 722192 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@H:4]([C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25](O)=[O:26])=[CH:21][CH:20]=3)=[CH:15][CH:14]=1)=[O:11])[CH2:3]2.S(Cl)([Cl:30])=O.[NH3:32]>C1COCC1>[ClH:30].[NH2:32][C:25]([C:22]1[CH:23]=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10]([C@@H:4]3[CH:5]4[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]4)[CH2:3]3)=[O:11])=[CH:14][CH:15]=2)=[CH:20][CH:21]=1)=[O:26]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 69617638HCID 69617638, compound

Product 1

HCID 69338674HCID 69338674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 mg (0.16 mmol) of 4′-{[(3S)-1-azabicyclo[2.2.2]oct-3-ylcarbonyl]amino}-1,1′-biphenyl-4-carboxylic acid hydrochloride and 2 ml (27.4 mmol) of thionyl chloride are heated under reflux for 3 h. The excess of thionyl chloride is distilled off. The crude acid chloride prepared in this way is introduced into 1 ml of THF and stirred with 3.1 ml (1.55 mmol) of ammonia (0.5M solution in dioxane) at RT for three days. The solvent is removed under reduced pressure, and the crude product is purified by preparative HPLC. 11 mg (18% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 3 h
  2. distillationThe excess of thionyl chloride is distilled off
  3. customThe crude acid chloride prepared in this way
  4. customThe solvent is removed under reduced pressure
  5. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-1297b391d8a04b128e5356cf69454ac6
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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