4-Methylphenyl isocyanate → 1-(4-Methylphenyl)-3-{4-[4-morpholin-4-yl-6-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1,3,5-triazin-2-yl]phenyl}urea

HRID 536805Notes

Reaction equation

HRID 536805 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([N:13]3[CH2:19][CH:18]4[O:20][CH:15]([CH2:16][CH2:17]4)[CH2:14]3)[N:10]=[C:9]([C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:28]1([CH3:37])[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>CN(C1C=CN=CC=1)C>[CH3:37][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:25][C:24]2[CH:26]=[CH:27][C:21]([C:9]3[N:8]=[C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[N:12]=[C:11]([N:13]4[CH2:14][CH:15]5[O:20][CH:18]([CH2:17][CH2:16]5)[CH2:19]4)[N:10]=3)=[CH:22][CH:23]=2)=[O:36])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 670218524-[4-Morpholin-4-yl-6-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1,3,5-triazin-2-yl]aniline

Product 1

HCID 445483021-(4-Methylphenyl)-3-{4-[4-morpholin-4-yl-6-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1,3,5-triazin-2-yl]phenyl}urea

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The titled compound was prepared by starting from 4-[4-morpholin-4-yl-6-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1,3,5-triazin-2-yl]aniline (100 mg, 0.27 mmol)-4-tolylisocyanate (60 mg, 0.45 mmol) and DMAP (5 mg) was stirred at room temperature for a period of 24 hours. At the end, reaction mixture was concentrated and purified by Gilson HPLC, using ACN/water and TFA. White solid; mp: 228; Yield 80 mg (80%); (M+H) 502.4

Workup

  1. customAt the end, reaction mixture
  2. concentrationwas concentrated
  3. custompurified by Gilson HPLC

Sources & evidence

ORD record
ord-ce648d6be2cf44e7a525add8af7ee875
Source dataset
uspto-grants-2014_10
Patent number
US08859542B2

Reaction notes

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