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 339678Notes

Reaction equation

HRID 339678 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22]([C:25]2[N:29]4[CH:30]=[CH:31][C:32]([CH:34]=[O:35])=[CH:33][C:28]4=[N:27][N:26]=2)[CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].N.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO.CC(O)C.CC(O)=O>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22]([C:25]2[N:29]4[CH:30]=[CH:31][C:32]([CH2:34][OH:35])=[CH:33][C:28]4=[N:27][N:26]=2)[CH:21]=[CH:20]3)[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

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-0282a01cc8ec4b15bf42c83c9a889cb5
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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