Ethanolamine → HCID 66686018, compound

HRID 1697385

Reaction equation

[CH2:1]([CH2:3][NH2:4])[OH:2].[CH:5]1([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH2:34][C@H:35]5[CH2:37][O:36]5)[CH2:26][CH2:25]4)[C:18]3=[O:38])[CH:11]=2)[CH2:7][CH2:6]1>CN(C=O)C>[CH:5]1([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[O:33][CH2:34][C@H:35]([OH:36])[CH2:37][NH:4][CH2:3][CH2:1][OH:2])[CH2:25][CH2:26]4)[C:18]3=[O:38])[CH:11]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 50 °C

Procedure

Ethanolamine (1 mL) was added to N-cyclopropyl-4-methyl-3-{3-[(1-{2-[(2R)-oxiran-2-ylmethoxy]phenyl}cyclopropyl)amino]-2-oxopyrazin-1(2H)-yl}benzamide (Example 299a, 7.81 g) in DMF (3 mL). The reaction was heated at 50° C. overnight. The reaction mixture was partitioned between water and DCM. The combined organics were dried (MgSO4), filtered and evaporated. Purification by preparative HPLC (Xbridge column, eluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia) gave the title product (0.102 g) after solvent removal and trituration with diethyl ether.

Workup

customThe reaction mixture was partitioned between water and DCM
dry with materialThe combined organics were dried (MgSO4)
filtrationfiltered
customevaporated
customPurification by preparative HPLC (Xbridge column
washeluting with a gradient of acetonitrile in 0.2% (v/v) aqueous ammonia)

Sources & evidence

ORD record: ord-9dec82a4ed2545a5b8ea095ad73c4cd5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163905B2

Linked notes

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