3-Bromopyridine → (S)-tert-butyl 4-(4-(1-(2-methylpyridin-3-yl)pyrrolidine-3-carboxamido)phenyl)piperidine-1-carboxylate

HRID 873582Notes

Reaction equation

HRID 873582 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:8]1[CH2:12][CH2:11][C@H:10]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)=[O:14])[CH2:9]1.N1CC(C(NC2C=CC(OC3CCN(C(OC(C)(C)C)=O)CC3)=CC=2)=O)[CH2:36]1>>[CH3:36][C:3]1[C:2]([N:8]2[CH2:12][CH2:11][C@H:10]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH:22]4[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]4)=[CH:20][CH:21]=3)=[O:14])[CH2:9]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 122863-BromopyridineHCID 86702036Tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylateHCID 86702068(S)-tert-butyl 4-(4-(pyrrolidine-3-carboxamido)phenyl)piperidine-1-carboxylate

Product 1

HCID 86702067(S)-tert-butyl 4-(4-(1-(2-methylpyridin-3-yl)pyrrolidine-3-carboxamido)phenyl)piperidine-1-carboxylate

Procedure

The title compound was prepared as described in Example 1C, substituting 3-bromo-2-methylpyridine for 3-bromopyridine and (S)-tert-butyl 4-(4-(pyrrolidine-3-carboxamido)phenyl)piperidine-1-carboxylate for tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate.

Sources & evidence

ORD record
ord-44255d1f42b2471f882bd63977605955
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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