Diisopropylethylamine → HCID 69099470, compound

HRID 2251477Notes

Reaction equation

HRID 2251477 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[C:31]1[N:36]=[CH:35][C:34]([Br:37])=[CH:33][N:32]=1.CCN(C(C)C)C(C)C>>[Br:37][C:34]1[CH:33]=[N:32][C:31]([N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=2)[CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=2)=[N:36][CH:35]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 109555882,5-DibromopyrimidineHCID 59643115HCID 59643115, compound

Product 1

HCID 69099470HCID 69099470, compoundYield 37%

Procedure

Condensation of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (5.16 g; 12.6 mmol) with 2,5-dibromo-pyrimidine (3.0 g; 10.5 mmol) as per general procedure E (conditions: 1.1 eq DIEA, 210C, 2 hr) provided after chromatography the intermediate ethyl 2-[4-(2-{(5-bromopyrimidin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (2.2 g; 37% yield).

Sources & evidence

ORD record
ord-f73d2c1840e5400ea6bffe7205729a5f
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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