Ammonia → Tert-butyl(1-(2-(7-(hydroxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 1041966Notes

Reaction equation

HRID 1041966 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[C:15]([N:22]5[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24][CH2:23]5)[CH:16]=[CH:17][CH:18]=4)[N:13]=3)=[N:10][N:11]=[C:5]2[CH:4]=1)=[O:2].N.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO.CC(O)C.CC(O)=O>[C:32]([O:31][C:30](=[O:36])[NH:29][CH2:28][CH:25]1[CH2:24][CH2:23][N:22]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[N:13]=[C:12]([C:9]2[N:6]4[CH:7]=[CH:8][C:3]([CH2:1][OH:2])=[CH:4][C:5]4=[N:11][N:10]=2)[CH:21]=[CH:20]3)[CH2:27][CH2:26]1)([CH3:35])([CH3:33])[CH3:34]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 5049666Sodium triacetoxyborohydrideHCID 86654350Tert-butyl (1-(2-(7-formyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 131730903Tert-butyl(1-(2-(7-(hydroxymethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamateYield 29.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To tert-butyl (1-(2-(7-formyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (10 mg, 0.021 mmol) in DCM/MeOH (1 mL/1 mL) was added NH3 in IPA (0.1 mL, 2M) and HOAc (0.2 mL), followed by NaB(OAc)3H (13 mg, 0.062 mmol). The reaction was stirred for 5 hours and then concentrated. The crude material was purified by silica gel chromatography (DCM/MeOH/NH4OH 20:1:0.1) to provide the desired product (3 mg). MS ESI (+) m/z 489 (M+1) detected.

Workup

  1. concentrationconcentrated
  2. customThe crude material was purified by silica gel chromatography (DCM/MeOH/NH4OH 20:1:0.1)

Sources & evidence

ORD record
ord-c61a78c532b84278b906b74dcdf8ae1c
Source dataset
uspto-grants-2013_10
Patent number
US08557809B2

Reaction notes

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