Trimethylsilyldiazomethane → HCID 46869423, compound

HRID 2098068Notes

Reaction equation

HRID 2098068 reaction equation
[C:1]([C:3]1[C:4]([C:23]2[N:27]=[CH:26][NH:25][N:24]=2)=[C:5]([NH:8][C:9](=[O:22])[CH2:10][N:11]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][C:12]2=[O:21])[S:6][CH:7]=1)#[N:2].[Si](C=[N+]=[N-])(C)(C)[CH3:29]>CO.C(Cl)Cl>[C:1]([C:3]1[C:4]([C:23]2[N:27]=[CH:26][N:25]([CH3:29])[N:24]=2)=[C:5]([NH:8][C:9](=[O:22])[CH2:10][N:11]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][C:12]2=[O:21])[S:6][CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 178510537HCID 178510537, compound

Product 1

HCID 46869423HCID 46869423, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

N-(4-cyano-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)acetamide (180 mg, 0.475 mmol) was dissolved in MeOH/CH2Cl2 (1:1, 4 mL total), and TMSCHN2 (Aldrich, 2.0 M in diethyl ether, 8 mL, 16 mmol) was added at rt. This was stirred for 4 h, whereupon the reaction mixture was concentrated under reduced pressure. The crude residue was purified by HPLC to give a white solid as a trifluoroacetic acid salt: method [11], retention time=7.56 min; MS (ESI) 394.2 (MH+); 1H NMR (300 MHz, CD3OD) 8.41 (s, 1H), 8.25 (d, J=5.0 Hz, 1H), 7.87 (s, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.52-7.42 (m, 1H), 4.98 (s, 2H), 3.97 (s, 3H), 3.40-3.20 (m, 2H), 2.96 (t, J=8.3 Hz, 2H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe crude residue was purified by HPLC

Sources & evidence

ORD record
ord-ddc572e551314d768f4f15b36414b87f
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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