4-(N-Boc-amino)piperidine → HCID 67055953, compound

HRID 2036828Notes

Reaction equation

HRID 2036828 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[N:10][C:11]([C:17]2[CH:18]=[C:19]([C:23]4[N:27]=[C:26]([C:28](OC)=[O:29])[O:25][N:24]=4)[CH:20]=[N:21][CH:22]=2)=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:40]([NH:47][CH:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>C(O)C>[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[N:10][C:11]([C:17]2[CH:18]=[C:19]([C:23]4[N:27]=[C:26]([C:28]([N:51]5[CH2:50][CH2:49][CH:48]([NH:47][C:40](=[O:41])[O:42][C:43]([CH3:45])([CH3:44])[CH3:46])[CH2:53][CH2:52]5)=[O:29])[O:25][N:24]=4)[CH:20]=[N:21][CH:22]=2)=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7238334-(N-Boc-amino)piperidineHCID 51029808HCID 51029808, compound

Product 1

HCID 67055953HCID 67055953, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,2,4-oxadiazole-5-carboxylate (from example 187, 0.2 g, 0.38 mmol) in ethanol (10 mL) was added 4-(Boc-amino)piperidine (0.389 g, 1.90 mmol). Upon completion of addition, the reaction mixture was heated to 80° C. where it stirred for 16 h. At the conclusion of this period, the ethanol was evaporated and the resulting residue was purified by flash silica gel column chromatography (1.6% methanol in DCM) to yield tert-butyl 1-(3-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,2,4-oxadiazole-5-carbonyl)piperidin-4-ylcarbamate (0.1 g, 38% yield) as yellow solid. LCMS Method T: retention time 2.08 min; [M+1]=684.2.

Workup

  1. additionUpon completion of addition
  2. customAt the conclusion of this period, the ethanol was evaporated
  3. customthe resulting residue was purified by flash silica gel column chromatography (1.6% methanol in DCM)

Sources & evidence

ORD record
ord-a4e5227ae06c412eb860a47e3d13be93
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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