Trimethylsilyldiazomethane → HCID 59636662, compound

HRID 2098070Notes

Reaction equation

HRID 2098070 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[N:26]=[CH:25][NH:24][N:23]=2)=[C:4]([NH:7][C:8](=[O:21])[CH2:9][N:10]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][C:11]2=[O:20])[S:5][CH:6]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:28]>>[Cl:1][C:2]1[C:3]([C:22]2[N:26]=[CH:25][N:24]([CH3:28])[N:23]=2)=[C:4]([NH:7][C:8](=[O:21])[CH2:9][N:10]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][C:11]2=[O:20])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178521252HCID 178521252, compound

Product 1

HCID 59636662HCID 59636662, compound

Procedure

The titled compound was synthesized from N-(4-chloro-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide and TMSCHN2. HPLC purification afforded a white solid. LCMS method [11], retention time=7.322 min; MS (ESI) 403.2 (MH+, 35C1); 1H NMR (300 MHz, CD3OD) δ 8.43 (s, 1H), 8.29 (d, J=5.3 Hz, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.59 (t, J=7.1 Hz, 1H), 6.94 (s, 1H), 4.98 (s, 2H), 3.98 (s, 3H), 3.36 (t, J=7.5 Hz, 2H), 2.97 (dd, J=8.2, 6.3 Hz, 2H).

Workup

  1. customHPLC purification
  2. customafforded a white solid

Sources & evidence

ORD record
ord-e3218622d468474081e267599c3f7eec
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…