Sodium bis(trimethylsilyl)amide → HCID 59623745, compound

HRID 1093953Notes

Reaction equation

HRID 1093953 reaction equation
C[O:2][C:3]([C:5]1[C:10]([N:11]([CH2:20][CH:21]([F:23])[F:22])[S:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:14])=[O:13])=[N:9][CH:8]=[CH:7][N:6]=1)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>O1CCCC1>[CH3:19][O:18][C:16]([C:15]1[S:12](=[O:14])(=[O:13])[N:11]([CH2:20][CH:21]([F:23])[F:22])[C:10]2[C:5]([C:3]=1[OH:2])=[N:6][CH:7]=[CH:8][N:9]=2)=[O:17]

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 59623759HCID 59623759, compound

Product 1

HCID 59623745HCID 59623745, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(2,2-difluoro-ethyl)-methoxycarbonylmethanesulfonyl-amino]-pyrazine-2-carboxylic acid methyl ester (Example 9.2) (0.819 g) in tetrahydrofuran (40 ml) under nitrogen atmosphere was added in portions a solution of sodium hexamethyldisilazide (“NaHMDS”) (5.8 ml) (1M in THF) at ambient temperature. The reaction mixture was stirred for 3 hours at ambient temperature. The reaction was quenched by addition of glacial acetic acid and the mixture was concentrated. The residue was partitioned between ethyl acetate (30 ml) and aqueous hydrochloric acid (2M) (15 ml). The phases were separated and the organic layer was concentrated to give 1-(2,2-difluoro-ethyl)-4-hydroxy-2,2-dioxo-1,2-dihydro-2-λ-6-thia-1,5,8-triaza-naphthalene-3-carboxylic acid methyl ester (0.520 g). 1H-NMR (400 MHz, CDCl3): 8.65 (d, 1H), 8.59 (d, 1H), 6.02-6.32 (m, 1H), 4.60-4.67 (m, 2H), 4.13 (s, 3H) ppm.

Workup

  1. customThe reaction was quenched by addition of glacial acetic acid
  2. concentrationthe mixture was concentrated
  3. customThe residue was partitioned between ethyl acetate (30 ml) and aqueous hydrochloric acid (2M) (15 ml)
  4. customThe phases were separated
  5. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-50c41266080b4772bbaeb4c3c44c6874
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

Loading…