Diisopropylethylamine → HCID 10278979, compound

HRID 1815931Notes

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.[CH3:25]CN(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]([N:17]([CH3:25])[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

Reactant 3

HCID 81531Diisopropylethylamine

HCID 22496104N-(5-amino-2-methoxyphenyl)-acrylamide

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

Product 1

HCID 10278979HCID 10278979, 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) (90 mg, 0.256 mmol) in IpOH (3 ml) was added DIEA (0.067 mL, 0.385 mmol) and N-(5-amino-2-methoxy-phenyl)acrylamide (Example 12, Step 2) (54. mg, 0.282 mmol). The mixture 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-yl)-methyl-amino]-[1,3,5]triazin-2-ylamino}-2-methoxyphenyl)acrylamide: MS m/z=507 [M+H]+. Calc'd for C28H26N802: 506.22.

Workup

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

Sources & evidence

ORD record: ord-1543e77f57f34848be0898e6ae59189b
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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