Morpholine → HCID 58181682, compound

HRID 876632Notes

Reaction equation

HRID 876632 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CCN=C=NCCCN(C)C.Cl>CC#N.CN(C1C=CN=CC=1)C.CCOC(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:6]

Participants

7

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27789252-Fluoro-5-iodobenzoic acid

Product 1

HCID 58181682HCID 58181682, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Fluoro-5-iodobenzoic acid (2 g, 0.0088 mol) was dissolved in MeCN (44 ml) and the mixture cooled to 0° C. Morpholine (0.929 ml, 1.2 eq) followed by EDCI.HCl (2.03 g, 1.2 eq) and DMAP (108 mg, 0.1 eq) were added and the mixture stirred overnight. The mixture was diluted with EtOAc, washed with NH4Cl(sat), dried (MgSO4), and concentrated. The resulting residue was then purified by silica gel chromatography (0-30% EtOAc in hexane) gave 2 g of M1-5. LCMS MH+=336.

Workup

  1. additionwere added
  2. washwashed with NH4Cl(sat)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting residue was then purified by silica gel chromatography (0-30% EtOAc in hexane)
  6. customgave 2 g of M1-5

Sources & evidence

ORD record
ord-64d9a296351e49f3852643c363ed50cc
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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