HCID 68755461, compound → HCID 56668539, compound

HRID 2098138Notes

Reaction equation

HRID 2098138 reaction equation
[Br:1][C:2]1[C:3]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[C:4]([NH2:7])[S:5][CH:6]=1.[O:13]=[C:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]1[CH2:24][C:25](O)=[O:26]>>[Br:1][C:2]1[C:3]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)=[C:4]([NH:7][C:25](=[O:26])[CH2:24][N:15]2[C:16]3[C:21](=[N:20][CH:19]=[CH:18][CH:17]=3)[CH2:22][CH2:23][C:14]2=[O:13])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 68755461HCID 68755461, compoundHCID 68782483HCID 68782483, compound

Product 1

HCID 56668539HCID 56668539, compoundYield 15.3%

Procedure

The title compound was prepared from 4-bromo-3-(thiazol-2-yl)thiophen-2-amine (90 mg, 0.35 mmol) and 2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetic acid (105 mg, 0.52 mmol) according to protocol A. The crude product was purified by HPLC to give N-(4-bromo-3-(thiazol-2-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide (24 mg) as a white solid. LCMS m/z 449.0/451.0 and retention of 4.019 min using method [7]. 1H-NMR (300 MHz, CDCl3) δ 8.39 (d, J=5.2 Hz, 1H), 7.76 (d, J=3.3 Hz, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.51 (dd, J=8.4, 5.3 Hz, 1H), 7.34 (d, J=3.4, 1H), 6.94 (s, 1H), 4.09 (s, 2H), 3.49 (t, J=7.2 Hz, 2H), 3.00 (t, J=7.2 Hz, 2H).

Workup

  1. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-dbe6d91e2f78409fa94b68af89e1b415
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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