Isopropyl isocyanate → N-(2-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}-1,1-dimethylethyl)-N'-isopropylurea

HRID 540873Notes

Reaction equation

HRID 540873 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[NH2:7][C:8]([CH3:33])([CH3:32])[CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:29]([O-:31])=[O:30]>ClCCl>[CH2:22]([O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([NH:10][CH2:9][C:8]([NH:7][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])([CH3:33])[CH3:32])=[C:12]([N+:29]([O-:31])=[O:30])[CH:13]=[N:14]2)=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 67050934(2-Amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amine

Product 1

HCID 69507170N-(2-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}-1,1-dimethylethyl)-N'-isopropylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl isocyanate (2.05 mL, 20.9 mmol) was added to a stirred suspension of (2-amino-2-methylpropyl)(7-benzyloxy-3-nitroquinolin-4-yl)amine (prepared as described in Part A of Example 45, 6.95 g, 19.0 mmol) in dichloromethane (200 mL) at 0° C. After approximately 30 minutes, the reaction mixture was allowed to warm to room temperature and was stirred overnight. The solvent was removed under reduced pressure to afford 8.49 g of N-(2-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}-1,1-dimethylethyl)-N′-isopropylurea.

Workup

  1. customprepared
  2. customat 0° C
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-621550999b2d4188be4840bc0cc72905
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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