6-Isocyanato-2,3-dihydro-1,4-benzodioxine → N-(2-t-Butoxycarbonylaminophenyl)-4-[3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-1-[3-(4-methylpiperazin-1-yl)propyl]ureidomethyl]benzamide

HRID 658039Notes

Reaction equation

HRID 658039 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]=[C:12]=[O:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[C:14]([O:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29](=[O:48])[C:30]1[CH:35]=[CH:34][C:33]([CH2:36][NH:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]2)=[CH:32][CH:31]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>ClCCl>[C:14]([O:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29](=[O:48])[C:30]1[CH:35]=[CH:34][C:33]([CH2:36][N:37]([CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]2)[C:12]([NH:11][C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)=[O:13])=[CH:32][CH:31]=1)=[O:20])([CH3:16])([CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 27761726-Isocyanato-2,3-dihydro-1,4-benzodioxineHCID 58001232HCID 58001232, compound

Product 1

HCID 58000978N-(2-t-Butoxycarbonylaminophenyl)-4-[3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-1-[3-(4-methylpiperazin-1-yl)propyl]ureidomethyl]benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dihydrobenzo[1,4]dioxin-6-ylisocyanate (0.11 mL, 0.80 mmol) was added to a solution of N-(2-t-butoxycarbonylaminophenyl)-4-[3-(4-methylpiperazin-1-yl)propylaminomethyl]benzamide (Reference Compound No. 4-1, 350 mg, 0.73 mmol) in anhydrous dichloromethane (15 mL), and then the reaction mixture was stirred at room temperature for 40 minutes. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (chloroform-methanol) to give 460 mg of the title reference compound as a colorless amorphous product. (Yield 94%)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform-methanol)
  3. customto give 460 mg of the title reference compound as a colorless amorphous product

Sources & evidence

ORD record
ord-3185c90a22294db496219113bbba6498
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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