Potassium Bromide → HCID 178467515, compound

HRID 1591065Notes

Reaction equation

HRID 1591065 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([F:16])([F:15])[F:14])[CH:10]=2)[O:5][C:4]([CH3:18])([CH3:17])[C@H:3]1[OH:19].[CH2:20]([O:22][C:23]1[C:27](OCC)=[N:26][S:25](=[O:32])(=[O:31])[N:24]=1)[CH3:21].[K+].[Br-]>C(#N)C>[CH2:20]([O:22][C:23]1[C:27]([NH:1][C@@H:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([F:16])([F:14])[F:15])[CH:10]=3)[O:5][C:4]([CH3:17])([CH3:18])[C@H:3]2[OH:19])=[N:26][S:25](=[O:32])(=[O:31])[N:24]=1)[CH3:21]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 112179953,4-Diethoxy-1,2,5-thiadiazole-1,1-dioxideHCID 15020328(3S,4R)-4-Amino-2,2-dimethyl-6-(trifluoromethoxy)-chroman-3-ol

Product 1

HCID 178467515HCID 178467515, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3S, 4R)-4-Amino-2,2-dimethyl-6-(trifluoromethoxy)-chroman-3-ol [prepared by the method of Quagliato et al. Biorg. and Med. Chem. Let. 1991, 1, 39; (1.00 g, 3.61 mmol)] and the thiadiazole derivative (0.78 g, 3.79 mmol) obtained in Step 1 were stirred together in acetonitrile (15 mL) at 90° C. for 18 hours. The mixture was cooled and concentrated, and the residue was purified by column chromatography (1:1:05 hexane/ethyl acetate/dichloromethane) to give after trituration with hexanes 1.10 g (71%) of product as a white solid: mp 192°-194° C.; 1H NMR (DMSO-D6): δ 9.55 (d, 1H), 7.29 (d, 1H), 7.19 (d, 1H), 6.87 (d, 1H), 5.89 (d, 1H), 4.73 (t, 1H), 4.51 (q, 2H), 3.78 (m, 1H), 1.41 (t, 3 H), 1.38 (s, 3H), 1.15 (s, 3H); IR (KBr): 2500-3250, 1620, 1490 cm-1 ; MS (m/z) 438 (MH+, 100%), 261 (20).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customthe residue was purified by column chromatography (1:1:05 hexane/ethyl acetate/dichloromethane)
  4. customto give after trituration with hexanes 1.10 g (71%) of product as a white solid

Sources & evidence

ORD record
ord-ca908fd4976840548bc69496b3eacdf6
Source dataset
uspto-grants-1993_04
Patent number
US05206252

Reaction notes

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