Trimethylsilyl isocyanate → HCID 58190587, compound

HRID 1959682Notes

Reaction equation

HRID 1959682 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([O:6]/[N:7]=[C:8](/[C:10]2[N:15]=[C:14]3[N:16]([CH2:19][C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][C:29]=4[F:30])[N:26]=[CH:25][CH:24]=[CH:23]5)[N:17]=[N:18][C:13]3=[N:12][CH:11]=2)\[CH3:9])[CH2:2]1.[N:31]([Si](C)(C)C)=[C:32]=[O:33]>CCO>[F:30][C:29]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][CH:25]=[N:26]2)=[CH:21][C:20]=1[CH2:19][N:16]1[C:14]2=[N:15][C:10](/[C:8](=[N:7]/[O:6][C@H:3]3[CH2:4][CH2:5][N:1]([C:32]([NH2:31])=[O:33])[CH2:2]3)/[CH3:9])=[CH:11][N:12]=[C:13]2[N:18]=[N:17]1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 58190549HCID 58190549, compound

Product 1

HCID 58190587HCID 58190587, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S,E)-1-(1-((7-fluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-pyrrolidin-3-yl oxime (example 19) (20.0 mg, 0.05 mmol) in EtOH (5 mL) was added isocyanatotrimethylsilane (7.9 mg, 0.07 mmol). The mixture was stirred overnight. The solvent was removed under reduced pressure. The residue was diluted with MeOH (3 mL) and filtered. The filtrate was purified on HPLC (basic with 0.05% NH4OH) to give the title compound as a white solid (15.0 mg, 64%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.31 (s, 1H), 8.92 (dd, 1H), 8.40 (d, 1H), 8.17 (d, 1H), 7.82 (d, 1H), 7.53 (dd, 1H), 6.23 (s, 2H), 5.77 (s, 2H), 4.99 (m, 1H), 3.59 (d, 1H), 3.51-3.47 (m, 1H), 3.44-3.38 (m, 1H), 3.28-3.23 (m, 1H), 2.26 (s, 3H), 2.18-2.17 (m, 2H). LCMS (method A): [MH]+=450, tR=4.38 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with MeOH (3 mL)
  3. filtrationfiltered
  4. customThe filtrate was purified on HPLC (basic with 0.05% NH4OH)

Sources & evidence

ORD record
ord-d69a12fedfa047aaadc810316b24748c
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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