Hydrochloric Acid → HCID 71737326, compound

HRID 1842006Notes

Reaction equation

HRID 1842006 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]2[CH2:11][N:12]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C@@H:24]4[O:33][C:28]5=[N:29][CH:30]=[CH:31][CH:32]=[C:27]5[O:26][CH2:25]4)=[CH:20][CH:19]=3)[CH2:13][CH2:14][C:15]=2[N:16]=1)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl.CO>[O:26]1[C:27]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[O:33][C@@H:24]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][N:12]3[CH2:13][CH2:14][C:15]4[N:16]=[C:8]([NH2:7])[S:9][C:10]=4[CH2:11]3)=[CH:23][CH:22]=2)[CH2:25]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86695364HCID 86695364, compound2×

Product 1

HCID 71737326HCID 71737326, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of {5-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl}-carbamic acid tert-butyl ester (prepared from Intermediate N according to General Method K) (50 mg, 0.10 mmol) in DCM (2 mL) with several drops MeOH is added 4M HCl in 1,4-dioxane (1.0 mL, 4.0 mmol) and the reaction stirred at rt for 16 h. The reaction is concentrated, suspended in Et2O and filtered to give the title compound 258. (LC/MS method 16: ES+ m/z 381.4 [M+H]+, Rt=0.36 m)

Workup

  1. concentrationThe reaction is concentrated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-51d98a5b90594458a396cd204836b36a
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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