4-Benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylic acid → 4-benzyl-N-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

HRID 1676359Notes

Reaction equation

HRID 1676359 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)=[O:23])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:32])[CH:3]=1.[CH2:33]([N:40]1[CH:45]=[CH:44][N:43]=[C:42]([C:46](O)=[O:47])[C:41]1=[O:49])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([N:40]1[CH:45]=[CH:44][N:43]=[C:42]([C:46]([NH:1][C:2]2[CH:31]=[CH:30][C:5]([O:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[CH:13]=[C:14]([C:16]5[CH:17]=[CH:18][C:19]([C:22]([N:24]6[CH2:25][CH2:26][O:27][CH2:28][CH2:29]6)=[O:23])=[CH:20][CH:21]=5)[S:15][C:8]=34)=[C:4]([F:32])[CH:3]=2)=[O:47])[C:41]1=[O:49])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

3

Reactant 2

HCID 673467874-Benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylic acidHCID 67347265(4-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)(morpholino)methanone

Product 1

HCID 589494504-benzyl-N-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-oxo-3,4-dihydropyrazine-2-carboxamideYield 45%

Procedure

Prepared from (4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)(morpholino)methanone (Example 129, Step A) and 4-benzyl-3-oxo-3,4-dihydropyrazine-2-carboxylic acid according to the procedure of Example 89. The crude was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2) to afford 12 mg (45%) of the desired product. LRMS (APCI pos) m/e 662.2 (M+1). 1H-NMR (400 MHz, CDCl3/CD3OD) δ 8.03 (dd, 1H), 7.96 (d, if H), 7.92 (d, 2H), 7.85 (s, if H), 7.77 (d, 1H), 7.56 (m, 3H), 7.36-7.46 (m, 7H), 6.66 (d, 1H), 5.33 (s, 2H), 3.68-3.81 (m, 8H); 19F NMR (376 MHz, CDCl3/CD3OD) δ −128.2.

Workup

  1. customThe crude was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-73283a15983d40a4b3c852a93e3e8ff2
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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