Water → HCID 117892068, compound

HRID 930550Notes

Reaction equation

HRID 930550 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH3:10])[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[OH:30][CH:31]1[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]1.O>C1COCC1>[CH3:37][N:34]1[CH2:35][CH2:36][CH:31]([O:30][C:2]2[N:7]=[C:6]([NH:8][CH:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH3:10])[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=2)[CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 962WaterHCID 660484-Piperidinol, 1-methyl-HCID 3251421Potassium bis(trimethylsilyl)amideHCID 43524568HCID 43524568, compound

Product 1

HCID 117892068HCID 117892068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

6-chloro-3-nitro-N-[1-(pyridin-2-yl)ethyl]pyridin-2-amine E-3.8″(2 g; 7.17 mmol) is suspended in 20 ml THF and a potassium bis(trimethylsilyl)amide solution in THF (29 ml; 29 mmol) is slowly added at 25° C. After 15 min 4-hydroxy-N-methylpiperidine (3.37 g; 28.71 mmol) is added and the reaction mixture is stirred for 16 h at 25° C. The reaction mixture is diluted with ethyl acetated and water. The organic phase is separated and dried using MgSO4. The crude intermediate is purified using reversed phase chromatography (prep. HPLC1). The product containing fractions are combined and freeze-dried

Workup

  1. additionThe reaction mixture is diluted with ethyl
  2. customThe organic phase is separated
  3. customdried
  4. customThe crude intermediate is purified
  5. additionThe product containing fractions
  6. customfreeze-dried

Sources & evidence

ORD record
ord-8d7eb0be73044f32a31dd6911c9fe88a
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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