Diisopropylethylamine → N-{5-[4-(1-benzyl-1H-indazol-5-ylamino)-[1,3,5]triazin-2-ylamino]-2-methoxyphenyl}-acrylamide

HRID 1815930Notes

Reaction equation

HRID 1815930 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[N:23]=[C:22](Cl)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[NH2:34][C:35]1[CH:36]=[CH:37][C:38]([O:46][CH3:47])=[C:39]([NH:41][C:42](=[O:45])[CH:43]=[CH2:44])[CH:40]=1>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:34][C:35]4[CH:36]=[CH:37][C:38]([O:46][CH3:47])=[C:39]([NH:41][C:42](=[O:45])[CH:43]=[CH2:44])[CH:40]=4)[N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 22496104N-(5-amino-2-methoxyphenyl)-acrylamideHCID 22496107(1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)amine

Product 1

HCID 10300180N-{5-[4-(1-benzyl-1H-indazol-5-ylamino)-[1,3,5]triazin-2-ylamino]-2-methoxyphenyl}-acrylamide

Conditions

Temperature
100 °C

Procedure

To a slurry of (1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)-amine (Example 3, Step 3) (90 mg, 0.267 mmol) in IpOH (3 ml) was added DIEA (0.070 mL, 0.401 mmol) and N-(5-amino-2-methoxyphenyl)acrylamide (Step 2) (56.5 mg, 0.294 mmol). The mix was heated at 100° C. for 18 h. The solution was then cooled to RT. A precipitate fell out of solution, was filtered off and dried under reduced pressure to give N-{5-[4-(1-benzyl-1H-indazol-5-ylamino)-[1,3,5]triazin-2-ylamino]-2-methoxyphenyl}-acrylamide: MS m/z=493[M+H]+. Calc'd for C27H24N8O2: 492.20.

Workup

  1. temperatureThe solution was then cooled to RT
  2. filtrationwas filtered off
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-bfc8c9f648004d2e96e3cbb5fb8f3f76
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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