Isopropyl isocyanate → HCID 58742395, compound

HRID 722195Notes

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.[CH:26]([N:29]=[C:30]=[O:31])([CH3:28])[CH3:27]>C1COCC1.CN(C=O)C>[CH:26]([NH:29][C:30](=[O:31])[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)([CH3:28])[CH3:27]

Participants

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. 17 mg (0.21 mmol) of isopropyl 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. 23 mg (52% of theory) of the title compound are obtained.

Workup

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

Sources & evidence

ORD record: ord-a65d3c7e6402485a8b52877f5526d044
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138410B2

Reaction notes

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