2-Methoxyethylamine → HCID 67410229, compound

HRID 909380Notes

Reaction equation

HRID 909380 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]([CH:15]2[C:24]3[C:23](=[O:25])[CH2:22][CH:21]([CH2:26][CH2:27][CH3:28])[CH2:20][C:19]=3[NH:18][C:17]([CH3:29])=[C:16]2[C:30]#[N:31])[CH:12]=[C:11]([O:32][CH2:33][CH3:34])[C:3]=1[O:4][CH2:5][CH:6]=[CH:7][C:8](O)=[O:9].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:68][O:69][CH2:70][CH2:71][NH2:72]>ClCCl.O>[CH3:68][O:69][CH2:70][CH2:71][NH:72][C:8](=[O:9])[CH:7]=[CH:6][CH2:5][O:4][C:3]1[C:11]([O:32][CH2:33][CH3:34])=[CH:12][C:13]([CH:15]2[C:24]3[C:23](=[O:25])[CH2:22][CH:21]([CH2:26][CH2:27][CH3:28])[CH2:20][C:19]=3[NH:18][C:17]([CH3:29])=[C:16]2[C:30]#[N:31])=[CH:14][C:2]=1[Br:1]

Participants

7

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67410399HCID 67410399, compound

Product 1

HCID 67410229HCID 67410229, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[2-bromo-4-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydroquinolin-4-yl)-6-ethoxy-phenoxy]-but-2-enoic acid (0.1 g), HATU (0.108 g), DiPEA (165 μl) and 2-methoxyethylamine (25 μl) in dichloromethane was stirred for 2 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by preparative HPLC (Method B). Yield: 65.5 mg. MS-ESI: [M+H]+=586.4/588.4; HPLC: Rt=16.39 min. (method 1). Diast. ratio: 5:1

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (Method B)

Sources & evidence

ORD record
ord-23ccb2587c30425899dc72941a465184
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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