Hydrochloric Acid → HCID 68110238, compound

HRID 1503967Notes

Reaction equation

HRID 1503967 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([O:16][CH:17]4[CH2:22][CH2:21][CH:20]([N:23](C)[C:24](=O)OC(C)(C)C)[CH2:19][CH2:18]4)[C:6]=3[C:5]1=2.Cl.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:24][NH:23][CH:20]1[CH2:21][CH2:22][CH:17]([O:16][C:7]2[C:6]3[C:5]4[C@@H:4]([CH2:3][CH2:2][OH:1])[CH2:15][CH2:14][C:13]=4[S:12][C:11]=3[N:10]=[CH:9][N:8]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86695135HCID 86695135, compound

Product 1

HCID 68110238HCID 68110238, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

For the preparation of the starting material compound 34.2, please refer to the experimental procedure for the synthesis of compound Example 34. A 50-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a solution of tert-butyl N-(4-[[(3R)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (197 mg, 0.44 mmol, 1.00 equiv) in dichloromethane (15 mL). Hydrochloric acid (conc., 0.5 mL) was added at 0° C. and the resulting solution was stirred for 2 h at room temperature. The pH value of the solution was adjusted to 10 with aqueous sodium bicarbonate (sat.) and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]ethan-1-ol (118 mg, 77%) as a yellow solid. MS (ES): m/z 348[M+H]+.

Workup

  1. customplease refer to the experimental procedure for the synthesis of compound Example 34
  2. customA 50-mL round-bottom flask, purged
  3. temperaturemaintained with an inert atmosphere of nitrogen
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dadc73ff2d1046ff8a9ccdb70ff7d2ac
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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