Trimethylsilyl isocyanate → HCID 58190501, compound

HRID 1892365Notes

Reaction equation

HRID 1892365 reaction equation
[NH2:1][CH2:2][CH2:3][O:4]/[N:5]=[C:6](/[C:8]1[N:13]=[C:12]2[N:14]([CH2:17][C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][CH:22]=[CH:21]4)[N:15]=[N:16][C:11]2=[N:10][CH:9]=1)\[CH3:7].C[Si]([N:32]=[C:33]=[O:34])(C)C>C(Cl)Cl>[N:24]1[C:25]2[C:20](=[CH:19][C:18]([CH2:17][N:14]3[C:12]4=[N:13][C:8](/[C:6](=[N:5]/[O:4][CH2:3][CH2:2][NH:1][C:33]([NH2:32])=[O:34])/[CH3:7])=[CH:9][N:10]=[C:11]4[N:16]=[N:15]3)=[CH:27][CH:26]=2)[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 58190489HCID 58190489, compound

Product 1

HCID 58190501HCID 58190501, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-2-aminoethyl oxime (example 34) (15 mg, 0.041 mmol) in DCM (5 mL) was added trimethylsilyl isocyanate (19.07 mg, 0.166 mmol). The mixture was stirred for 24 h. After concentration, the crude product was purified by chromatography on silica gel to afford 11.6 mg (69%) of the title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.32 (s, 1H), 8.89 (dd, 1H), 8.35 (d, 1H), 8.01 (m, 2H), 7.82 (d, 1H), 7.53 (dd, 1H), 6.21 (s, 2H), 6.05 (t, 1H), 5.50 (s, 2H), 4.27 (t, 2H), 3.35 (m, 2H), 2.32 (s, 3H). LCMS (method B): [MH]+=406, tR=1.91 min.

Workup

  1. concentrationAfter concentration
  2. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c08b69a5188c4d74980cbe061821c697
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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