Water → HCID 86653129, compound

HRID 1258573Notes

Reaction equation

HRID 1258573 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.[H-].[Na+].Br[CH2:34][CH2:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.O>CN(C=O)C.CCOC(C)=O>[CH:36]1([CH2:35][CH2:34][N:23]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:16][O:15][N:14]=[C:7]([C:6]3[N:2]([CH3:1])[N:3]=[N:4][N:5]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:22]=2)[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 962WaterHCID 15440(2-Bromoethyl)cyclohexaneHCID 24758Sodium hydrideHCID 76469643HCID 76469643, compound

Product 1

HCID 86653129HCID 86653129, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (0.2 g, 0.488 mmol, 1 eq.) in 3 ml of dry DMF was treated with NaH (60% dispn in mineral oil, 0.020 g, 0.513 mmol, 1.05 eq.) added in one portion. After 20 mins (2-bromoethyl)cyclohexane (0.098 g, 0.513 mmol, 1.05 eq.) was added and the reaction was stirred for 1 hr. Water was added followed by EtOAc. The aqueous layer was separated and extracted with EtOAc. Then the organics were combined, dried over MgSO4 and evaporated to give tert-butyl (2-cyclohexylethyl){6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (0.27 g, 85%) as a viscous oil

Workup

  1. additionadded in one portion
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-b2dfa0b3ce644485bfa101470ce9a830
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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