Ethanolamine → HCID 66686039, compound

HRID 337152Notes

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[CH2:6][CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([NH:18][C:19]1[C:20](=[O:39])[N:21]([C:25]2[CH:26]=[C:27]([CH:34]=[C:35]([F:38])[C:36]=2[CH3:37])[C:28]([NH:30][CH:31]2[CH2:33][CH2:32]2)=[O:29])[CH:22]=[CH:23][N:24]=1)([CH3:17])[CH3:16]>>[CH:31]1([NH:30][C:28](=[O:29])[C:27]2[CH:26]=[C:25]([N:21]3[CH:22]=[CH:23][N:24]=[C:19]([NH:18][C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[S:8][CH2:7][CH2:6][NH:4][CH2:3][CH2:1][OH:2])([CH3:17])[CH3:16])[C:20]3=[O:39])[C:36]([CH3:37])=[C:35]([F:38])[CH:34]=2)[CH2:32][CH2:33]1

Participants

Reactant 2

HCID 700Ethanolamine

HCID 66690768HCID 66690768, compound

Product 1

HCID 66686039HCID 66686039, compound

Procedure

The title compound was prepared from ethanolamine and 3-{3-[(1-{2-[(2-chloroethyl)sulfanyl]phenyl}-1-methylethyl)amino]-2-oxopyrazin-1(2H)-yl}-N-cyclopropyl-5-fluoro-4-methylbenzamide (Example 321a) using a similar method to that described for Example 252l. The crude product was purified by preparative HPLC (X-Bridge column eluting with 95-5% gradient of aqueous 0.2% ammonia in acetonitrile) to give the title compound as a solid.

Workup

customThe crude product was purified by preparative HPLC (X-Bridge column eluting with 95-5% gradient of aqueous 0.2% ammonia in acetonitrile)

Sources & evidence

ORD record: ord-3dc46014d8664d4e8ac8510e6ef6e5d2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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