Methyl Isocyanate → HCID 58742398, compound

HRID 722194Notes

Reaction equation

HRID 722194 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([C@@H:18]3[CH:23]4[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]4)[CH2:19]3)=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:26][N:27]=[C:28]=[O:29]>C1COCC1.CN(C=O)C>[CH3:26][NH:27][C:28](=[O:29])[O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([C@@H:18]3[CH:23]4[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]4)[CH2:19]3)=[O:17])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 58742399HCID 58742399, compound

Product 1

HCID 58742398HCID 58742398, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

35 mg (0.10 mmol) of (3R)-N-[4′-(hydroxymethyl)-1,1′-biphenyl-4-yl]-1-azabicyclo-[2.2.2]octane-3-carboxamide are dissolved in 1 ml of a 1:1 THF/DMF mixture. 12 mg (0.21 mmol) of methyl isocyanate are added, and the mixture is stirred at 60° C. overnight. The solvent is removed under reduced pressure, and the crude product is purified by preparative HPLC. 20 mg (49% of theory) of the title compound are obtained.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-6bbe8f76535648b4ab5c49b84f98b5c1
Source dataset
uspto-grants-2006_11
Patent number
US07138410B2

Reaction notes

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