Hydrochloric Acid → HCID 68819007, compound

HRID 656930Notes

Reaction equation

HRID 656930 reaction equation
[C:1]([C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:40])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]([CH2:29][C:30]3[N:35]=[CH:34][C:33]4[O:36][CH2:37][CH2:38][O:39][C:32]=4[CH:31]=3)C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1)#[N:2].[ClH:41].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)C>[ClH:41].[O:39]1[C:32]2[CH:31]=[C:30]([CH2:29][NH:21][CH:18]3[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:10]4[C:11]5[N:12]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=5[CH:7]=[CH:8][C:9]4=[O:40])[CH2:20][CH2:19]3)[N:35]=[CH:34][C:33]=2[O:36][CH2:37][CH2:38]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86635320HCID 86635320, compound

Product 1

HCID 68819007HCID 68819007, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1,1-dimethylethyl {1-[2-(7-cyano-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)carbamate (600 mg, 1.100 mmol) in DCM (10 ml) at 0° C. was added 1M HCl in diethyl ether (10 ml) and the reaction was stirred at 0° C. for 0.5 h and then allowed warm to rt and stirred at rt for 2 h before evaporation, treatment with sat. aq NaHCO3 (50 ml). The reaction was then extracted with 20% MeOH in DCM (3×200 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient to provide the free base of the title compound (314 mg, 64%).

Workup

  1. temperatureallowed warm to rt
  2. extractionThe reaction was then extracted with 20% MeOH in DCM (3×200 ml)
  3. customThe combined organic phases were dried
  4. customevaporated
  5. customthe crude residue purified by chromatography on silica gel using a 0-20% MeOH/DCM gradient

Sources & evidence

ORD record
ord-32aa3432a208462598e2678ef27611bf
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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