Methylamine → HCID 57771603, compound

HRID 2070577Notes

Reaction equation

HRID 2070577 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][C:19]3([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:18]2)=[CH:11][CH:10]=1)[C:6](O)=[O:7].Cl.[CH2:30]([N:32]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.CN>CN(C)C=O.O.O1CCCC1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][C:19]3([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:18]2)=[CH:11][CH:10]=1)[C:6]([NH:32][CH3:30])=[O:7]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57771424HCID 57771424, compound

Product 1

HCID 57771603HCID 57771603, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(spiro[5.5]undec-2-ylmethoxy)-phenyl]-succinic acid 4-methyl ester (310 mg) obtained in Step 6 in N,N-dimethylformamide (4 mL) were added successively 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (163 mg), 1-hydroxybenzotriazole hydrate (115 mg) and a tetrahydrofuran solution of methylamine (2M, 0.53 mL), followed by stirring the reaction mixture at room temperature for 13 hours. Then, after addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with 1N aqueous hydrochloric acid solution, water, saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:1) to give N-methyl-3-[4-(spiro[5.5]undec-2-ylmethoxy)-phenyl]-succina mic acid methyl ester (278 mg).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with 1N aqueous hydrochloric acid solution, water, saturated aqueous sodium bicarbonate solution and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:1)

Sources & evidence

ORD record
ord-97fcd1ef01ff4f6c899f721f79d1b161
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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