Triethylamine → 4-({[4-(4-{4-[(Methylcarbamoyl)amino]phenyl}-6-morpholin-4-yl-1,3,5-triazin-2-yl)phenyl]carbamoyl}amino)benzamide

HRID 404492Notes

Reaction equation

HRID 404492 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][CH3:30])=[O:28])=[CH:22][CH:21]=3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38]([C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:48](=[O:56])OC2C=CC=CC=2)=[CH:43][CH:42]=1)(=[O:40])[NH2:39]>CN(C=O)C>[CH3:30][NH:29][C:27]([NH:26][C:23]1[CH:22]=[CH:21][C:20]([C:10]2[N:11]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:13]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:48]([NH:47][C:44]4[CH:43]=[CH:42][C:41]([C:38]([NH2:39])=[O:40])=[CH:46][CH:45]=4)=[O:56])=[CH:7][CH:6]=3)[N:9]=2)=[CH:25][CH:24]=1)=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60631229Phenyl 4-carbamoylphenylcarbamateHCID 674385231-(4-(4-(4-Aminophenyl)-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-methylurea

Product 1

HCID 665855264-({[4-(4-{4-[(Methylcarbamoyl)amino]phenyl}-6-morpholin-4-yl-1,3,5-triazin-2-yl)phenyl]carbamoyl}amino)benzamideYield 5.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-(4-(4-aminophenyl)-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-methylurea (0.6 g, 1.5 mmol) and triethylamine (4-5 mL) in dry DMF (10 mL), phenyl 4-carbamoylphenylcarbamate (1.15 g, 4.5 mmol).) was added at room temperature and mixture was heated to 90° C. for 10 hours under nitrogen atmosphere. After cooling to room temperature reaction mixture was quenched with ice water and resulting solid was filtered to get crude product. Crude product was purified by Preparative HPLC to give 4-({[4-(4-{4-[(methylcarbamoyl)amino]phenyl}-6-morpholin-4-yl-1,3,5-triazin-2-yl)phenyl]carbamoyl}amino)benzamide (45 mg, 5.3% yield).

Workup

  1. addition) was added at room temperature
  2. temperatureAfter cooling to room temperature
  3. customreaction mixture
  4. customwas quenched with ice water
  5. customresulting solid
  6. filtrationwas filtered
  7. customto get crude product
  8. customCrude product was purified by Preparative HPLC

Sources & evidence

ORD record
ord-e8305ec00dd344b08eca61298e9f71b0
Source dataset
uspto-grants-2014_06
Patent number
US08748421B2

Reaction notes

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