Dimethylformamide → HCID 59216558, compound

HRID 386488

Reaction equation

HRID 386488 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:15][CH2:14]1.CCN(CC)CC.CN(C=O)C>O>[Cl:12][C:4]1[N:3]=[C:2]([N:13]2[CH2:14][CH2:15][CH:16]([NH:19][C:20](=[O:26])[O:21][CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:17][CH2:18]2)[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2986251,3-DichloroisoquinolineHCID 15676964HCID 15676964, compound

Product 1

HCID 59216558HCID 59216558, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1,3-dichloroisoquinoline (0.16 g, 0.78 mmol), isobutyl piperidin-4-ylcarbamate (0.16 g, 0.78 mmol), Et3N (0.11 mL, 0.78 mmol), and DMF (0.5 mL) was sealed in a microwave vessel and heated by microwave irradiation at 160° C. for three minutes. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield isobutyl 1-(3-chloroisoquinolin-1-yl)piperidin-4-ylcarbamate. LC/MS: m/z 362.2 (M+H)+ at 3.98 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas sealed in a microwave vessel
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12e5f6bc9b594acc8a4aca313eb831ae
Source dataset
uspto-grants-2013_02
Patent number
US08372843B2

Linked notes

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