5-Amino-4-(benzo[d]thiazol-2-yl)thiophene-3-carbonitrile → N-(3-(benzo[d]thiazol-2-yl)-4-cyanothiophen-2-yl)-2-(2-oxo-1,5-naphthyridin-1(2H)-yl)acetamide

HRID 2098145Notes

Reaction equation

HRID 2098145 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[N:3]1[CH2:12][C:13]([OH:15])=O.[NH2:16][C:17]1[S:21][CH:20]=[C:19]([C:22]#[N:23])[C:18]=1[C:24]1[S:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1>>[S:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[C:18]1[C:19]([C:22]#[N:23])=[CH:20][S:21][C:17]=1[NH:16][C:13](=[O:15])[CH2:12][N:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]1=[O:1]

Participants

3

Reactant 2

HCID 687573945-Amino-4-(benzo[d]thiazol-2-yl)thiophene-3-carbonitrileHCID 687824352-(2-oxo-1,5-naphthyridin-1(2H)-yl)acetic acid

Product 1

HCID 59636674N-(3-(benzo[d]thiazol-2-yl)-4-cyanothiophen-2-yl)-2-(2-oxo-1,5-naphthyridin-1(2H)-yl)acetamide

Procedure

The title compound was prepared from 2-(2-oxo-1,5-naphthyridin-1(2H)-yl)acetic acid (0.040 g, 0.19 mmol) and 5-amino-4-(benzo[d]thiazol-2-yl)thiophene-3-carbonitrile (0.073 g, 0.28 mmol) according to protocol A. The crude product was purified by prep HPLC. LCMS retention time (min)=5.122, method [12], MS (ESI) 446.1 (M+H). 1H NMR (CDCl3) δ 13.38 (s, 1H), 8.32 (d, J=5.6 Hz, 1H), 7.99 (d, J=7.5 Hz, 1H), 7.94 (d, J=7.5 Hz, 1H), 7.62 (s, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.47-7.42 (m, 1H), 7.35-7.30 (m, 1H), 4.95 (s, 2H), 3.33-3.28 (m, 2H), 2.99-2.94 (m, 2H).

Workup

  1. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-bc15cba62ae745fda31043f4297cbdf4
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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