Pyridine → N-(3-(1H-tetrazol-5-yl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 2098378Notes

Reaction equation

HRID 2098378 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH:12][C:13]([C:15]3([CH3:28])[CH2:20][CH2:19][N:18]([C:21](OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[O:14])[CH:9]=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1.C(OC(N1CCC(C)(C(O)=O)CC1)=O)(C)(C)C.[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(Cl)(=O)C(Cl)=O.[NH:58]1[C:62](C2C=C(N)C=CC=2)=[N:61]N=N1>ClC(Cl)C.CN(C=O)C>[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH:12][C:13]([C:15]3([CH3:28])[CH2:20][CH2:19][N:18]([C:21]4[C:50]5[C:48]([CH3:49])=[CH:47][NH:46][C:51]=5[N:58]=[CH:62][N:61]=4)[CH2:17][CH2:16]3)=[O:14])[CH:9]=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1

Participants

8

Reactant 5

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 178451883tert-butyl 4-(3-(1H-tetrazol-5-yl)phenylcarbamoyl)-4-methylpiperidine-1-carboxylateHCID 178507542HCID 178507542, compound

Product 1

HCID 178430821N-(3-(1H-tetrazol-5-yl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

Preparation of tert-butyl 4-(3-(1H-tetrazol-5-yl) phenylcarbamoyl)-4-methylpiperidine-1-carboxylate. To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (100 mg, 0.41 mmol) in dichloroethane (2.0 mL) were added DMF (2 drops) and pyridine (0.13 g, 1.6 mmol), followed by oxalyl chloride (57 mg, 0.45 mmol). The mixture was stirred for 40 minutes, and 3-(1H-tetrazol-5-yl)-phenylamine was added. The mixture was stirred for 2 hours, and a pink precipitate formed. The mixture was filtered, and the filtrate was washed with 1.0 N aq. HCl and brine, dried over MgSO4, and concentrated to give the title compound in 70% yield. MS (ES+) [M+H]+=387.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customa pink precipitate formed
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with 1.0 N aq. HCl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d162513bbcd4a0683d0ad05d111630f
Source dataset
uspto-grants-2013_05
Patent number
US08450332B2

Reaction notes

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