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

HRID 1815919Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:13]=[CH:12]3)[N:3]=1.CCN(C(C)C)C(C)C.[NH2:34][C:35]1[CH:36]=[C:37]([NH:41][C:42](=[O:45])[CH:43]=[CH2:44])[CH:38]=[CH:39][CH:40]=1>>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([NH:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:34][C:35]4[CH:36]=[C:37]([NH:41][C:42](=[O:45])[CH:43]=[CH2:44])[CH:38]=[CH:39][CH:40]=4)[N:3]=3)=[CH:17][CH:16]=2)[CH:12]=[N:13]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 22033841N-(3-Aminophenyl)acrylamide

HCID 22496124HCID 22496124, compound

Product 1

HCID 20775675N-{3-[4-(1-pyridin-2-ylmethyl-1H-indazol-5-ylamino)-[1,3,5]triazin-2-ylamino]-phenyl}-acrylamide

Conditions

Temperature: 100 °C

Procedure

To a slurry of (4-chloro-[1,3,5]triazin-2-yl)-(1-pyridin-2-ylmethyl-1H-indazol-5-yl)-amine (Step 3) (90.0 mg, 0.266 mmol) in IpOH (3.0 ml) was added DIEA (0.07 mL, 0.40 mmol) and N-(3-aminophenyl)acrylamide (47.5 mg, 0.293 mmol). The mix was heated at 100° C. for 18 h. The solution was cooled to RT. A precipitate fell out of solution, was filtered off and dried under reduced pressure to give N-{3-[4-(1-pyridin-2-ylmethyl-1H-indazol-5-ylamino)-[1,3,5]triazin-2-ylamino]-phenyl}-acrylamide: MS m/z=464[M+H]+. Calc'd for C25H21N9O: 463.19.

Workup

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

Sources & evidence

ORD record: ord-0ad3e87403264a1b8fee59ae8854d5ab
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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