Acetic Acid → Tert-butyl(1-(2-(7-((ethylamino)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 339679Notes

Reaction equation

HRID 339679 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)=[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].[CH2:37]([NH2:39])[CH3:38].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO>[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][NH:39][CH2:37][CH3:38])=[CH:33][C:28]4=[N:27][N:26]=2)[CH:21]=[CH:20]3)[CH2:13][CH2:14]1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 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 91546827Tert-butyl(1-(2-(7-((ethylamino)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 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 (Example 11, steps A-K; 10 mg, 0.021 mmol) in DCM/MeOH (1 mL/1 mL) was added EtNH2 (0.1 mL, 2M in THF) and HOAc (0.2 mL), followed by NaB(OAc)3H (13 mg, 0.062 mmol). The reaction mixture was stirred for 5 hours at ambient temperature and then concentrated. The crude material was purified by silica gel chromatography (DCM/MeOH/NH4OH 20:1:0.1) to provide the desired product (4 mg). MS APCI (+) m/z 343 (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-4ce59c482abb498f9cb88789af5d8924
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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