Sodium triacetoxyborohydride → 6-benzyl-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine

HRID 713220Notes

Reaction equation

HRID 713220 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:18]=[CH:17][C:16]2[C:11](=[N:12][C:13]([NH:34][CH:35]([CH3:37])[CH3:36])=[C:14]([N:19]3[CH2:24][CH2:23][CH:22]([O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[F:33])[CH2:21][CH2:20]3)[N:15]=2)[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:2]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:34][CH:35]([CH3:37])[CH3:36])=[C:14]([N:19]3[CH2:24][CH2:23][CH:22]([O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[F:33])[CH2:21][CH2:20]3)[N:15]=2)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 1181593286-Benzyl-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-3-(isopropylamino)pyrido[3,4-b]pyrazin-6-ium bromide

Product 1

HCID 1181593036-benzyl-2-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amineYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-benzyl-2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-3-(isopropylamino)pyrido[3,4-b]pyrazin-6-ium bromide (7.2 g, 12.62 mmol) in DCM (126 ml) was added NaBH(OAc)3 (16.05 g, 76 mmol). The resulting solution was stirred at room temperature for 3 days. After DCM was removed under vacuum, EtOAc (200 mL) was added to re-dissolve the residue. Then saturated NaHCO3 (150 mL) was added and the mixture was vigorously stirred for 30 min. The organic layer was washed with water (50 mL) and brine (50 mL), and dried with anhydrous Na2SO4 overnight. Removal of the solvent gave the title compound (6.43 g) as a yellow solid, which was used without further purification. ESI-MS m/z [M+H]+ 494.10.

Workup

  1. customAfter DCM was removed under vacuum, EtOAc (200 mL)
  2. additionwas added
  3. dissolutionto re-dissolve the residue
  4. additionThen saturated NaHCO3 (150 mL) was added
  5. stirringthe mixture was vigorously stirred for 30 min
  6. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  7. dry with materialdried with anhydrous Na2SO4 overnight
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-dbf74839b38d4ed49ca2d6b0e4167ffb
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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