Triethylamine → HCID 68997033, compound

HRID 657089Notes

Reaction equation

HRID 657089 reaction equation
[ClH:1].Cl.[NH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]2[C:17]3[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=3[N:15]=[N:14][C:13]2=[O:24])[CH2:6][CH2:5]1.C(N(CC)CC)C.[O:32]1[C:41]2[CH:40]=[C:39]([CH:42]=O)[N:38]=[CH:37][C:36]=2[O:35][CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[ClH:1].[O:32]1[C:41]2[CH:40]=[C:39]([CH2:42][NH:3][CH:4]3[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][N:12]4[C:17]5[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=5[N:15]=[N:14][C:13]4=[O:24])[CH2:6][CH2:5]3)[N:38]=[CH:37][C:36]=2[O:35][CH2:34][CH2:33]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 68992727HCID 68992727, compound

Product 1

HCID 68997033HCID 68997033, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-[2-(4-amino-1-piperidinyl)ethyl]-6-(methyloxy)-1,2,4-benzotriazin-3(4H)-one dihydrochloride (42 mg, 0.112 mmol) in chloroform (2 ml) and MeOH (0.1 ml) was treated with triethylamine (50 μl, 0.358 mmol) and stirred for 0.25 h before addition of 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde (for a synthesis see WO2004058144, Example 2(c) or WO03/087098, Example 19(d)) (18 mg, 0.112 mmol). The reaction was stirred for 0.5 h before addition of NaBH(OAc)3 (71 mg, 0.336 mmol). The reaction was stirred for 1 h before addition of sat. aq NaHCO3 (10 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 (26 mg, 51%).

Workup

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

Sources & evidence

ORD record
ord-0ddf78ef06c84cb89c950ebc964e617e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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