tert-Butyl isocyanate → N-(tert-butyl)-4-((1R,2S)-2-(2-(4-(1H-tetrazol-1-yl)phenoxy)ethyl)cyclopropyl)piperidine-1-carboxamide

HRID 1850769Notes

Reaction equation

HRID 1850769 reaction equation
[N:1]1([C:6]2[CH:23]=[CH:22][C:9]([O:10][CH2:11][CH2:12][C@@H:13]3[CH2:15][C@@H:14]3[CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.CCN(C(C)C)C(C)C.[C:33]([N:37]=[C:38]=[O:39])([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C>[C:33]([NH:37][C:38]([N:19]1[CH2:20][CH2:21][CH:16]([C@H:14]2[CH2:15][C@H:13]2[CH2:12][CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[N:4][N:3]=[N:2]3)=[CH:23][CH:22]=2)[CH2:17][CH2:18]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 81531DiisopropylethylamineHCID 867111854-((1R,2S)-2-(2-(4-(1H-tetrazol-1-yl)phenoxy)ethyl)cyclopropyl)piperidine

Product 1

HCID 70856344N-(tert-butyl)-4-((1R,2S)-2-(2-(4-(1H-tetrazol-1-yl)phenoxy)ethyl)cyclopropyl)piperidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-((1R,2S)-2-(2-(4-(1H-tetrazol-1-yl)phenoxy)ethyl)cyclopropyl)piperidine (20 mg, 0.064 mmol) in DMF (0.7 ml) under nitrogen at RT was added DIPEA (0.022 ml, 0.128 mmol) followed by t-butyl isocyanate (drop). At 20 minutes, LC/MS showed no SM left. Quenched with formic acid (4.90 μl, 0. The fractions containing product were collected and dried via GenoVac to afford the title compound. GPR119 Human EC50: 14.7 nM

Workup

  1. waitleft
  2. customQuenched with formic acid (4.90 μl, 0
  3. additionThe fractions containing product
  4. customwere collected
  5. customdried via GenoVac

Sources & evidence

ORD record
ord-6774ea93b18a48b1ae6a87a3235951ee
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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