Methylamine → HCID 57088947, compound

HRID 278499Notes

Reaction equation

HRID 278499 reaction equation
[OH:1][C@H:2]([C@H:4]([N:17]1[CH:21]=[C:20]([C:22]([O:24]C)=O)[N:19]=[CH:18]1)[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:3].[CH3:26][NH2:27]>O1CCCC1.ClCCl>[CH3:26][NH:27][C:22]([C:20]1[N:19]=[CH:18][N:17]([C@H:4]([CH2:5][CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[C@@H:2]([OH:1])[CH3:3])[CH:21]=1)=[O:24]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 70156280HCID 70156280, compound

Product 1

HCID 57088947HCID 57088947, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 1-[(2S,3R)-2-hydroxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxylate (obtained in Example 23(7))(25 mg) and methylamine (40% in water; 1 ml) in tetrahydrofuran (3 ml) was heated in a steel sealed tube at 120° C. overnight. The mixture was taken up in dichloromethane, washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (30:1) to give a white powder of N-methyl-1-[(2S,3R)-2-hydroxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamide (18.6 mg).

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (30:1)

Sources & evidence

ORD record
ord-d95711207516474d925df96d7309105d
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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