Hydrofluoric Acid → HCID 11299219, compound

HRID 1355452Notes

Reaction equation

HRID 1355452 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[S:16][C:17]([C:20]#[N:21])=[CH:18][N:19]=2)[CH:9]=1)(C)(C)C.F>C1COCC1>[OH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[S:16][C:17]([C:20]#[N:21])=[CH:18][N:19]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 1317239462-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamino]-thiazole-5-carbonitrile

Product 1

HCID 11299219HCID 11299219, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamino]-thiazole-5-carbonitrile (1.30 g, 3.75 mmol) was dissolved in 10 mL anh THF. Hydrogen-fluoride (Aldrich, 5.0 mL) was added and the reaction was stirred for 20 min. The bulk of the solvent was removed in vacuo and the resulting residue was diluted with half-saturated NaHCO3 (aq). A precipitate formed which was filtered and washed with water to afford the titled compound. 1H NMR (DMSO-d6) δ12.23 (bs, 1H), 8.30 (d, 1H, J=5.3 Hz), 8.26 (s, 1H), 7.15 (s, 1H), 6.99 (d, 1H, J=5.3 Hz), 5.49 (t, 1H, J=5.7 Hz) 4.54 (d, 2H, J=5.7 Hz).

Workup

  1. customThe bulk of the solvent was removed in vacuo
  2. additionthe resulting residue was diluted with half-saturated NaHCO3 (aq)
  3. customA precipitate formed which
  4. filtrationwas filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-ac2dcc25cb9b498dab3264792b0160a8
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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