3-Aminobenzamide → 3-{1-[4-(3,4,5-trimethoxy-phenylamino)-[1,3,5]triazin-2-yl]-1H-benzoimidazol-2-ylamino}-benzamide

HRID 983445Notes

Reaction equation

HRID 983445 reaction equation
Cl[C:2]1[N:6]([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[N:8]=2)[C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[N:3]=1.[NH2:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([NH2:36])=[O:35].CCN(C(C)C)C(C)C>>[CH3:25][O:24][C:16]1[CH:15]=[C:14]([NH:13][C:9]2[N:10]=[CH:11][N:12]=[C:7]([N:6]3[C:5]4[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=4[N:3]=[C:2]3[NH:30][C:31]3[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=3)[C:34]([NH2:36])=[O:35])[N:8]=2)[CH:19]=[C:18]([O:20][CH3:21])[C:17]=1[O:22][CH3:23]

Participants

4

Reactant 3

HCID 16453-AminobenzamideHCID 81531DiisopropylethylamineHCID 22560111[4-(2-Chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)amine

Product 1

HCID 235357873-{1-[4-(3,4,5-trimethoxy-phenylamino)-[1,3,5]triazin-2-yl]-1H-benzoimidazol-2-ylamino}-benzamide

Conditions

Temperature
115 °C

Procedure

A mixture of [4-(2-chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)amine (Example 1, step 1)(41 mg, 0.10 mmol), 3-aminobenzamide (14 mg, 0.10 mmol) and DIEA (16 mg, 0.12 mmol) in IpOH (3.5 mL) was heated at 100-130° C. for 10-40 h. On cooling a precipitate formed which was collected, washed with IpOH, ether and dried to give 3-{1-[4-(3,4,5-trimethoxy-phenylamino)-[1,3,5]triazin-2-yl]-1H-benzoimidazol-2-ylamino}-benzamide as a yellow solid.

Workup

  1. temperatureOn cooling a precipitate
  2. customformed which
  3. customwas collected
  4. washwashed with IpOH, ether
  5. customdried

Sources & evidence

ORD record
ord-bf86112d7b9b4298a3fd372765890b39
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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