Butyl isocyanate → HCID 67059654, compound

HRID 1807736Notes

Reaction equation

HRID 1807736 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:23]([N:27]=[C:28]=[O:29])[CH2:24][CH2:25][CH3:26]>CN(C)C=O.ClCCl.CO>[CH2:16]([N:13]1[CH2:12][CH2:11][N:10]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:28]([NH:27][CH2:23][CH2:24][CH2:25][CH3:26])=[O:29])=[N:7][CH:6]=2)=[O:9])[CH2:15][CH2:14]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 67059707HCID 67059707, compound

Product 1

HCID 67059654HCID 67059654, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
100 °C

Procedure

(6-Aminopyridin-3-yl)(4-benzylpiperazin-1-yl)methanone (90 mg, 0.304 mmol) and n-butyl isocyanate (103 μl, 91 mg, 0.914 mmol) were combined in dimethylformamide (3 mL) and the mixture was heated to 100° C. for 6 hours. After this time the mixture was taken up in dichloromethane/methanol and loaded on to a strong cation exchange column (2 g) and washed with dichloromethane/methanol. Elution of the column with 2M ammonia in methanol gave a residue that was further purified by silica chromatography (eluting with 5% methanol/dichloromethane) to give the title compound (58 mg).

Workup

  1. washwashed with dichloromethane/methanol
  2. washElution of the column with 2M ammonia in methanol
  3. customgave a residue that
  4. customwas further purified by silica chromatography (eluting with 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5f64e295dd464c8f944b0df8d58f1cc2
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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