Diisopropylethylamine → (S)-N-(2-(2-(2,5,8,11,14,17,20,23-octaoxapentacosan-25-ylcarbamoyl)piperidin-1-yl)ethyl)-N3-(4-(diethylamino)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)-N1-methylisophthalamide

HRID 625466Notes

Reaction equation

HRID 625466 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]([NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])=[O:12].[CH2:39]([N:41]([CH2:80][CH3:81])[C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49]([C:51]2[CH:52]=[C:53]([CH:57]=[CH:58][CH:59]=2)[C:54]([OH:56])=O)=[O:50])=[C:44]([C:60]2[CH:65]=[C:64]([C:66](=[O:79])[NH:67][CH2:68][C:69]3[CH:74]=[CH:73][CH:72]=[C:71]([C:75]([F:78])([F:77])[F:76])[CH:70]=3)[CH:63]=[CH:62][N:61]=2)[CH:43]=1)[CH3:40].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:38][O:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][NH:13][C:11]([C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[C:54](=[O:56])[C:53]1[CH:57]=[CH:58][CH:59]=[C:51]([C:49]([NH:48][C:45]2[CH:46]=[CH:47][C:42]([N:41]([CH2:39][CH3:40])[CH2:80][CH3:81])=[CH:43][C:44]=2[C:60]2[CH:65]=[C:64]([C:66](=[O:79])[NH:67][CH2:68][C:69]3[CH:74]=[CH:73][CH:72]=[C:71]([C:75]([F:76])([F:77])[F:78])[CH:70]=3)[CH:63]=[CH:62][N:61]=2)=[O:50])[CH:52]=1)=[O:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66586873HCID 66586873, compoundHCID 66587742(S)-1-(2-(methylamino)ethyl)-N-(2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl)piperidine-2-carboxamide

Product 1

HCID 86709216(S)-N-(2-(2-(2,5,8,11,14,17,20,23-octaoxapentacosan-25-ylcarbamoyl)piperidin-1-yl)ethyl)-N3-(4-(diethylamino)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)-N1-methylisophthalamideYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of (S)-1-(2-(methylamino)ethyl)-N-(2,5,8,11,14,17,20,23-octaoxapentacosan-25-yl)piperidine-2-carboxamide (0.145 mmol), 3-((4-(diethylamino)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzoic acid (0.12 mmol, 80 mg) and DIEA (0.6 mmol, 78 mg) in DMF (0.4 mL) was added HATU (0.145 mmol, 55 mg). The mixture was stirred at 60° C. for 1 h and purified by prep. HPLC to give a yellow solid (91 mg, 52%). MS (ES, m/z): 1124.38 [M+H]+.

Workup

  1. custompurified by prep

Sources & evidence

ORD record
ord-e78d5eff86c74ff499e47f1bfbc1180f
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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