Hydrochloric Acid → HCID 9870142, compound

HRID 353533Notes

Reaction equation

HRID 353533 reaction equation
[OH:1][NH:2][C:3]([C:5]1([S:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]#[C:21][CH3:22])=[CH:14][CH:13]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[Br:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1.Cl>CO.C(OCC)(=O)C.CN(C)C=O>[OH:1][NH:2][C:3]([C:5]1([S:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]#[C:21][CH3:22])=[CH:16][CH:17]=2)[CH2:10][CH2:9][N:8]([CH2:35][C:34]2[CH:37]=[CH:38][C:31]([Br:30])=[CH:32][CH:33]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 9905160HCID 9905160, compound

Product 1

HCID 9870142HCID 9870142, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-But-2-ynyloxy-phenylsulfanyl)-piperidine-4-carboxylic acid hydroxy-amide (prepared by the procedure outlined in example 15) (0.15 g, 0.5 mmol) in methanol (5 mL) and dimethylformamide (2.5 mL) was treated with triethylamine (0.15 mL, 1.1 mmol) followed by 4-bromobenzylbromide (0.13 g, 0.53 mmol). After 6 h the solution was diluted with ethyl acetate, acidified to pH=6 with 1N aqueous hydrochloric acid, washed sequentially with water, aqueous sodium bicarbonate and brine and dried over anhydrous sodium sulfate. Concentration in vacuo gave 1-(4-bromo-benzyl)-4-(4-but-2-ynyloxy-phenylsulfanyl)-piperidine-4-carboxylic acid hydroxyamide. 1HNMR (DMSO-d6): 1.5-1.6 (m, CHH, 2H), 1.8 (s, CH3, 3H), 1.9-2.2 (m, CHH, 4H), 2.5-2.6 (m, CHH, 2H), 3.4 (s, CH2Ar, 2H), 4.75 (s, CH2, 2H), 6.9 (d, ArH, 2H), 7.2 (d, ArH, 2H), 7.3 (d, ArH, 2H), 7.5 (d, ArH, 2H), 8.8 (s, NHOH, 1H), 10.6 (d, NHOH, 1H). Electrospray Mass Spectroscopy: ((M+H)+=489/491).

Workup

  1. washwashed sequentially with water, aqueous sodium bicarbonate and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-13b7749cc0264598a2dfea4bebd5061c
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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