Diisopropylethylamine → HCID 10183167, compound

HRID 1815915Notes

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:40]=[CH:39][C:38]([NH:41][C:42](=[O:45])[CH:43]=[CH2:44])=[CH:37][CH:36]=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]([NH:41][C:42](=[O:45])[CH:43]=[CH2:44])=[CH:39][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

Reactant 3

HCID 81531Diisopropylethylamine

HCID 22496099N-(4-Aminophenyl)prop-2-enamide

HCID 22496107(1-benzyl-1H-indazol-5-yl)-(4-chloro-[1,3,5]triazin-2-yl)amine

Product 1

HCID 10183167HCID 10183167, compound

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) (80.0 mg, 0.238 mmol) in IpOH (3.0 ml) was added DIEA (0.062 mL, 0.356 mmol) and N-(4-aminophenyl)acrylamide (Example 2, Step 2) (42.4 mg, 0.261 mmol). The mix was heated at 100° C. for 18 h. The solution was then cooled to RT. A precipitate fells out of solution, was filtered off and dried under reduced pressure to give N-{4-[4-(1-benzyl-1H-indazol-5-ylamino)-[1,3,5]triazin-2-ylamino]-phenyl}-acrylamide: MS m/z=463[M+H]+. Calc'd for C26H22N8O: 462.19.

Workup

temperatureThe solution was then cooled to RT
filtrationwas filtered off
customdried under reduced pressure

Sources & evidence

ORD record: ord-d62a7015d7a9450fac86617225ea75cb
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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