tert-Butyl isocyanate → HCID 117992837, compound

HRID 717089Notes

Reaction equation

HRID 717089 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[CH:15][CH:14]=1)[NH:6][C:7]2=[O:12].[C:26]([N:30]=[C:31]=[O:32])([CH3:29])([CH3:28])[CH3:27]>C(Cl)Cl>[C:26]([NH:30][C:31]([N:23]1[CH2:24][CH2:25][N:20]([CH2:19][C:16]2[CH:15]=[CH:14][C:13]([C:5]3[NH:6][C:7](=[O:12])[C:8]4[C:3]([CH:4]=3)=[C:2]([CH3:1])[CH:11]=[CH:10][CH:9]=4)=[CH:18][CH:17]=2)[CH2:21][CH2:22]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 71737385HCID 71737385, compound

Product 1

HCID 117992837HCID 117992837, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-methyl-3-(4-piperazin-1-ylmethyl-phenyl)-2H-isoquinolin-1-one (40 mg, 0.12 mmol) in CH2Cl2 (0.5 mL) was added tert-butyl isocyanate (0.014 mL, 0.12 mmol) and the reaction mixture stirred at RT for 1 h after which time the solvent was removed in vacuo and the crude residue purified by reverse phase preparative HPLC-MS to afford 4-[4-(5-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl)-benzyl]-piperazine-1-carboxylic acid tert-butylamide as a white solid (28 mg, 54%).

Workup

  1. customwas removed in vacuo
  2. customthe crude residue purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-58963f27f76f493787c68f18f1f30d06
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

Loading…