Hydrochloric Acid → HCID 56847990, compound

HRID 1038302Notes

Reaction equation

HRID 1038302 reaction equation
[F:1][C:2]([F:38])([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:36]=[CH:35][C:18]([CH2:19][NH:20][O:21][C@H:22]4[C@H:27]([O:28][CH3:29])[C@H:26]([O:30][CH3:31])[C@@H:25]([O:32][CH3:33])[C@H:24]([CH3:34])[O:23]4)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[ClH:39]>C(OCC)C>[ClH:39].[F:38][C:2]([F:1])([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:36]=[CH:35][C:18]([CH2:19][NH:20][O:21][C@H:22]4[C@H:27]([O:28][CH3:29])[C@H:26]([O:30][CH3:31])[C@@H:25]([O:32][CH3:33])[C@H:24]([CH3:34])[O:23]4)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56847989HCID 56847989, compound

Product 1

HCID 56847990HCID 56847990, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of N-{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzyl}-O-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl)-hydroxylamine (3; 87.5 mg, 0.162 mmol) in diethyl ether (Et2O; 8.75 mL) was treated by the dropwise addition of HCl (4 M in dioxane) until no more solid precipitated. The resulting suspension was spun in a centrifuge and the solvent was decanted. The solid was slurried with fresh Et2O, centrifuged and the solvent was decanted. The resulting solid was dried by evaporation at room temperature under vacuum to give the title product (70 mg, 75%) as a white solid: mp 107-121° C.; 1H NMR (300 MHz, CD3OD) δ 9.46 (d, J=2.8 Hz, 1H), 8.37-8.17 (m, 2H), 8.15-7.96 (m, 2H), 7.73 (d, J=8.3 Hz, 2H), 7.63-7.41 (m, 2H), 5.45 (d, J=2.4 Hz, 1H), 4.75-4.58 (m, 2H), 3.83-3.24 (m, 17H), 3.11 (dd, J=9.2, 8.3 Hz, 1H), 1.25 (d, J=6.2 Hz, 3H), 1.18 (td, J=7.2, 2.8 Hz, 2H); ESIMS m/z 539 (M+H, base).

Workup

  1. customprecipitated
  2. customthe solvent was decanted
  3. customcentrifuged and the solvent was decanted
  4. customThe resulting solid was dried by evaporation at room temperature under vacuum

Sources & evidence

ORD record
ord-47babe96ede341c8b744de312d4cd303
Source dataset
uspto-grants-2013_10
Patent number
US08551914B2

Reaction notes

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