2-Hydroxy-1-(morpholin-4-yl)ethan-1-one → HCID 178508781, compound

HRID 2170092Notes

Reaction equation

HRID 2170092 reaction equation
[NH2:1][C:2]1[C:3]([C:10](/[N:12]=[C:13]2/[NH:14][C:15]3([CH2:22][CH2:21][N:20]([C:23](=[O:37])[CH2:24][CH2:25][C:26]4[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:28][CH:27]=4)[CH2:19][CH2:18]3)[CH2:16][NH:17]/2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.OCC(N1CCCC1C(F)(F)F)=O.O[CH2:52][C:53]([N:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1)=[O:54]>>[N:55]1([C:53](=[O:54])[CH2:52][O:33][C:32](=[O:34])[CH2:31][O:30][C:29]2[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][C:23]([N:20]3[CH2:21][CH2:22][C:15]4([NH:14]/[C:13](=[N:12]/[C:10]([C:3]5[C:2]([NH2:1])=[N:7][C:6]([NH2:8])=[C:5]([Cl:9])[N:4]=5)=[O:11])/[NH:17][CH2:16]4)[CH2:18][CH2:19]3)=[O:37])=[CH:36][CH:35]=2)[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1

Participants

4

Reactant 3

HCID 64804842-Hydroxy-1-(morpholin-4-yl)ethan-1-oneHCID 667975172-Hydroxy-1-(2-(trifluoromethyl)pyrrolidin-1-yl)ethanoneHCID 178508776[4-(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]dec-8-yl}-3-oxo-propyl)-phenoxy]-acetic acid2×

Product 1

HCID 178508781HCID 178508781, compound

Procedure

The title compound was prepared by an analogous method to Example 4.0, replacing 3-(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-propionic acid with [4-(3-{2-[(E)-3,5-diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]dec-8-yl}-3-oxo-propyl)-phenoxy]-acetic acid (Intermediate B), and 2-hydroxy-1-(2-(trifluoromethyl)pyrrolidin-1-yl)ethanone (Int. D) with 2-hydroxy-1-morpholin-4-yl-ethanone; 1H NMR (400 MHz, DMSO-d6) δ 8.40 (2H, br hump), 7.15 (2H, d), 6.87 (2H, d), 6.72 (2H, br s), 4.93 (2H, s), 4.82 (2H, s), 3.63 (2H, m), 3.56 (4H, m), 3.42 (2H, m), 3.40 (8H, m), 2.74 (2H, t), 2.59 (2H, t), 1.59 (4H, m). LC-MS Rt 3.10 mins; 658.4 [M+H]+, Method 10minLC_v002.

Sources & evidence

ORD record
ord-017f50b5465a4668bac9939cb8eb499a
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

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