Isocyanatocyclopropane → 1-Cyclopropyl-3-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-urea

HRID 524377

Reaction equation

HRID 524377 reaction equation
[N:1]1([C:7]2[CH:8]=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:24]1([N:27]=[C:28]=[O:29])[CH2:26][CH2:25]1>ClCCl>[CH:24]1([NH:27][C:28]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[N:9]=[CH:8][C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)=[N:16]4)=[CH:18][CH:19]=2)=[O:29])[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 637659IsocyanatocyclopropaneHCID 67034978HCID 67034978, compound

Product 1

HCID 670352451-Cyclopropyl-3-[4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenyl]-ureaYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3-morpholin-4-yl-quinoxalin-6-yl)-phenylamine [Intermediate Example 4.1] (100 mg) in dichloromethane (3.3 mL) was cooled (ice bath) and treated with cyclopropyl isocyanate (30 mg, 0.36 mmol) and stirred at room temperature for 3 days. The resulting precipitate was filtered, washed with dichloromethane and dried to give the title compound (96 mg). UPLC-MS: RT=1.01 min; m/z (ES+) 390.24 [MH+]; required MW=389.46.

Workup

  1. temperaturewas cooled (ice bath)
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with dichloromethane
  4. customdried

Sources & evidence

ORD record
ord-c8bf5d93196e40dd92f81856387d748b
Source dataset
uspto-grants-2016_05
Patent number
US09340528B2

Linked notes

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