Sodium Hydroxide → HCID 178461692, compound

HRID 1094332Notes

Reaction equation

HRID 1094332 reaction equation
Cl[C:2]1[C:3]([C@@H:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[S:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=3)=[CH:11][CH:10]=2)[CH3:8])=[N:4][S:5][N:6]=1.[OH-:25].[Na+]>CO>[F:22][C:21]([F:24])([F:23])[C:19]1[N:20]=[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([C@H:7]([C:3]3[C:2]([OH:25])=[N:6][S:5][N:4]=3)[CH3:8])=[CH:10][CH:11]=2)[S:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86645985HCID 86645985, compound

Product 1

HCID 178461692HCID 178461692, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Intermediate 14b (1.09 g, 2.80 mmol) was dissolved in a solution of NaOH (0.11 g, 2.75 mmol) in CH3OH (10 ml). The reaction mixture was stirred for 1 h at 50° C. and then quenched with a saturated solution of NH4Cl (10 ml); the aqueous layer was extracted with CH2Cl2 (2×10 ml) and the combined organic phases, after drying over anhydrous Na2SO4, were evaporated under vacuum and crystallized from n-heptane to give the pure 4-[(1R)-1-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)ethyl]-1,2,5-thiadiazol-3-ol (14) (0.625 g, 1.68 mmol) as a white solid (60%). [α]D=−33 (c=1; CH3OH); 1H-NMR (CDCl3): δ 9.25 (bs, 1H, NH), 8.35 (bs, 1H, OH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.00 (s, 1H), 3.85 (q, 1H, J=7 Hz) 1.75 (d, 3H, J=7 Hz).

Workup

  1. customquenched with a saturated solution of NH4Cl (10 ml)
  2. extractionthe aqueous layer was extracted with CH2Cl2 (2×10 ml)
  3. dry with materialthe combined organic phases, after drying over anhydrous Na2SO4
  4. customwere evaporated under vacuum
  5. customcrystallized from n-heptane

Sources & evidence

ORD record
ord-f41f6020ccf745a9844a47e003bbe4e7
Source dataset
uspto-grants-2012_03
Patent number
US08133911B2

Reaction notes

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