HCID 68782483, compound → HCID 178440438, compound

HRID 2098041Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:8]2[NH:12][N:11]=[C:10]([CH:13]([CH3:15])[CH3:14])[N:9]=2)=[C:4]([NH2:7])[S:5][CH:6]=1.[O:16]=[C:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][N:23]=2)[N:18]1[CH2:27][C:28](O)=[O:29]>>[Cl:1][C:2]1[C:3]([C:8]2[NH:12][N:11]=[C:10]([CH:13]([CH3:15])[CH3:14])[N:9]=2)=[C:4]([NH:7][C:28](=[O:29])[CH2:27][N:18]2[C:19]3[C:24](=[N:23][CH:22]=[CH:21][CH:20]=3)[CH2:25][CH2:26][C:17]2=[O:16])[S:5][CH:6]=1

Participants

Reactant 2

HCID 68782483HCID 68782483, compound

HCID 178440439HCID 178440439, compound

Product 1

HCID 178440438HCID 178440438, compound

Procedure

The title compound was prepared from 4-chloro-3-(3-isopropyl-1H-1,2,4-triazol-5-yl)thiophen-2-amine (117 mg, 482 umol) and 2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetic acid (155 mg, 752 umol) using protocol A and was purified by HPLC to yield N-(4-chloro-3-(3-isopropyl-1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide. Method [7] Retention time 0.35 min by HPLC (M+=431 and 433) and (M+Na=453 and 455). 1H NMR (300 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.30 (d, J=5.1 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 7.51 (m, 1H), 7.16 (d, J=1.8 Hz, 1H), 4.89 (s, 2H) 3.17 (m, 2H), 2.98 (m, 1H), 2.81 (m, 2H), 1.28 (d, J=7.2 Hz, 6H).

Workup

customwas purified by HPLC

Sources & evidence

ORD record: ord-0ebd5fed0012463f9accd4810682fc64
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450363B2

Reaction notes

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