HCID 68782483, compound → HCID 178438042, compound

HRID 2098043Notes

Reaction equation

HRID 2098043 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[NH:12][N:11]=[C:10]([CH2:13][CH3:14])[N:9]=2)=[C:4]([NH2:7])[S:5][CH:6]=1.[O:15]=[C:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][N:22]=2)[N:17]1[CH2:26][C:27](O)=[O:28]>>[Cl:1][C:2]1[C:3]([C:8]2[NH:12][N:11]=[C:10]([CH2:13][CH3:14])[N:9]=2)=[C:4]([NH:7][C:27](=[O:28])[CH2:26][N:17]2[C:18]3[C:23](=[N:22][CH:21]=[CH:20][CH:19]=3)[CH2:24][CH2:25][C:16]2=[O:15])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 68782483HCID 68782483, compoundHCID 178438043HCID 178438043, compound

Product 1

HCID 178438042HCID 178438042, compound

Procedure

The title compound was prepared from 4-chloro-3-(3-ethyl-1H-1,2,4-triazol-5-yl)thiophen-2-amine (18 mg, 78.7 umol) and 2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetic acid (20 mg, 97.0 umol) using protocol A. The residue was purified by HPLC to yield N-(4-chloro-3-(3-ethyl-1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide. Method [8] Retention time 4.47 min by HPLC (M+=417 and 419) and (M+Na=439 and 441). 1H NMR (300 MHz, CDCl3) δ 8.39 (dd, J=5.4 and 1.2 Hz, 1H), 7.67 (dd, J=8.1 and 1.2 Hz, 1H), 7.49 (dd, J=8.1 and 5.4 Hz, 1H), 6.85 (s, 1H), 4.93 (s, 2H), 3.49 (m, 2H), 3.01 (m, 2H), 2.84 (q, J=7.8 Hz, 2H), 1.39 (t, J=7.8 Hz, 3H).

Workup

  1. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-df07d7cc103740faa2378a919371153e
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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