Hydrochloric Acid → HCID 9913669, compound

HRID 1797273Notes

Reaction equation

HRID 1797273 reaction equation
[NH2:1][CH2:2][C@@H:3]([NH:19][C:20](=[O:33])[CH:21]=[CH:22][C:23]1[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:24]=1[O:31][CH3:32])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.Cl.C(N(CC)CC)C.[C:42](Cl)(=[O:44])[CH3:43]>C(Cl)Cl>[C:42]([NH:1][CH2:2][C@@H:3]([NH:19][C:20](=[O:33])/[CH:21]=[CH:22]/[C:23]1[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[CH:25][C:24]=1[O:31][CH3:32])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH2:7][CH2:6]1)(=[O:44])[CH3:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86592170HCID 86592170, compound

Product 1

HCID 9913669HCID 9913669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of E)-N-{(R)-1-aminomethyl-2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide.HCl salt (0.35 g, 0.66 mmol) and triethylamine (0.27 ml, 1.99 mmol) in DCM (5 ml) is treated with acetyl chloride (0.042 ml, 0.6 mmol) at 5° C. The reaction mixture is stirred at ambient temperature for 1 hour then washed with water, saturated aqueous NaHCO3 and brine. The organic phase is dried over MgSO4 and the solvent evaporated. The crude product is purified by flash chromatography (elution methanol:DCM; 4:96) to afford (E)-N-{(R)-1-(acetylamino-methyl)-2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide. [MH]+ 495.0.

Workup

  1. washthen washed with water, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent evaporated
  4. customThe crude product is purified by flash chromatography (elution methanol:DCM; 4:96)

Sources & evidence

ORD record
ord-526eb9beccc4427ca738f5c9f7da35c8
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

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