Ethylboronic acid → HCID 131736805, compound

HRID 1486713Notes

Reaction equation

HRID 1486713 reaction equation
Br[C:2]1C=CC([N+]([O-])=O)=C[C:3]=1C=O.[C:13](NC(C1CCNCC1)=O)(C)(C)[CH3:14].[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:41]=2Br)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C(B(O)O)C>>[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([NH2:46])[CH:43]=[CH:42][C:41]=2[CH2:2][CH3:3])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].[C:26]([NH:30][C:31]([CH:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[C:44]([N+:46]([O-:48])=[O:47])[CH:43]=[CH:42][C:41]=2[CH2:13][CH3:14])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 521157Ethylboronic acidHCID 7175833N-tert-butylpiperidine-4-carboxamideHCID 111389422-Bromo-5-nitrobenzaldehydeHCID 131736807HCID 131736807, compound

Product 2

HCID 131736805HCID 131736805, compoundHCID 131736806HCID 131736806, compound

Procedure

The title compound is prepared according to the reactions described above starting from 2-bromo-5-nitro-benzaldehyde and piperidine-4-carboxylic acid tert-butylamide yielding after reductive amination 1-(2-bromo-5-nitro-benzyl)-piperidine-4-carboxylic acid tert-butylamide; LC-MS A: tR=0.62 min; [M+H]+=397.99; followed by alkylation with ethylboronic acid yielding 1-(2-ethyl-5-nitro-benzyl)-piperidine-4-carboxylic acid tert-butylamide; LC-MS A: tR=0.66 min; [M+H]+=348.34, followed by reduction with stannous chloride the title compound; LC-MS A: tR=0.49 min; [M+H]+=318.21.

Sources & evidence

ORD record
ord-9ad1479c911d422a847323f8b24fae5e
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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