2-Methoxyethylamine → HCID 67437324, compound

HRID 1663380Notes

Reaction equation

HRID 1663380 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[C:17]3[C:16](=[O:18])[CH2:15][CH:14]([CH2:19][CH2:20][CH3:21])[CH2:13][C:12]=3[NH:11][C:10]([CH3:22])=[C:9]2[C:23]#[N:24])[CH:5]=[C:4]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[C:3]=1[NH:32][CH2:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([OH:40])=O)=[CH:36][CH:35]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:74][O:75][CH2:76][CH2:77][NH2:78]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[C:17]3[C:16](=[O:18])[CH2:15][CH:14]([CH2:19][CH2:20][CH3:21])[CH2:13][C:12]=3[NH:11][C:10]([CH3:22])=[C:9]2[C:23]#[N:24])[CH:5]=[C:4]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])[C:3]=1[NH:32][CH2:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH:78][CH2:77][CH2:76][O:75][CH3:74])=[O:40])=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67434806HCID 67434806, compound

Product 1

HCID 67437324HCID 67437324, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-{[2-bromo-4-(3-cyano-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinolin-4-yl)-6-(propane-1-sulfonylamino)-phenylamino]-methyl}-benzoic acid (200 mg), TBTU (300 mg), N,N-diisopropylethylamine (536 μl) and 2-methoxyethylamine (134 μl) in DMF (2 ml) was stirred for 2 h at room temperature. The mixture was diluted with ethyl acetate and washed with aq. NaHCO3.

Workup

  1. washwashed with aq. NaHCO3

Sources & evidence

ORD record
ord-562b65b8004943d2b035ec914f7b58d1
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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