tert-Butyl isocyanate → HCID 49763929, compound

HRID 1893239Notes

Reaction equation

HRID 1893239 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:17][CH:16]([NH:18][C:19]([CH2:21][NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=4)=[O:20])[CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:35]([N:39]=[C:40]=[O:41])([CH3:38])([CH3:37])[CH3:36]>CN(C=O)C>[C:35]([NH:39][C:40](=[O:41])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:15][CH:16]([NH:18][C:19]([CH2:21][NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=4)=[O:20])[CH2:17]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 49763806HCID 49763806, compound

Product 1

HCID 49763929HCID 49763929, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-({1-[4-(4-Amino-phenyl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (as prepared in Example 15, 100 mg, 0.21 mmol) in DMF (2 mL) was treated with t-butyl-isocyanate (Aldrich, 25 mg, 0.25 mmol) at room temperature for 48 hours. The reaction mixture was directly purified on a silica gel column using a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe reaction mixture was directly purified on a silica gel column

Sources & evidence

ORD record
ord-c015fdf5f41c470794e45d9e414dc7e2
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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