Methylamine → HCID 23627796, compound

HRID 1887216Notes

Reaction equation

HRID 1887216 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:28][C:29](O)=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CC[CH:35]([N:38]=C=NC2CCCCC2)CC1.C1COCC1.CN>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:28][C:29]([NH:38][CH3:35])=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 23627747HCID 23627747, compound

Product 1

HCID 23627796HCID 23627796, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of [(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-acetic acid (Example 59) (21.2 mg, 0.05 mmol) in CH2Cl2 (0.5 mL) at 0° C. was treated with DMAP (˜1 mg) and DCC (11.3 mg, 0.055 mmol) followed 5 min later by a 2 M THF solution of methylamine (30 μL, 0.06 mmol). The reaction mixture was stirred for 16 h, evaporated, and purified by silica gel flash chromatography with 50% EtOAc/hexane, then 100% EtOAc, then 5% Me0H/Et0Ac as eluant to afford product as an oil (6.4 mg, 29%). LC/MS 5.09 min, [M+1]+ 438.

Workup

  1. customevaporated
  2. custompurified by silica gel flash chromatography with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-e085a87176c74feba11fd247a8b2ad08
Source dataset
uspto-grants-2013_08
Patent number
US08501745B2

Reaction notes

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