Diisopropylethylamine → HCID 66586842, compound

HRID 625451Notes

Reaction equation

HRID 625451 reaction equation
C(N(CC)C1C=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)C(O)=O)=[O:12])=[C:6]([C:22]2[CH:27]=[C:26]([C:28](=[O:41])[NH:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[CH:25]=[CH:24][N:23]=2)C=1)C.CNC[CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58].[CH3:64][CH2:65][N:66]([CH:70]([CH3:72])C)[CH:67]([CH3:69])[CH3:68].CN([C:76]([O:80]N1N=NC2C=CC=NC1=2)=[N+:77]([CH3:79])[CH3:78])C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH2:70]([N:66]([CH2:65][CH3:64])[C:67]1[CH:68]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([C:76](=[O:80])[N:77]([CH3:78])[CH2:79][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH:19]=[CH:20][CH:21]=2)=[O:12])=[C:6]([C:22]2[CH:27]=[C:26]([C:28](=[O:41])[NH:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:39])([F:40])[F:38])[CH:32]=3)[CH:25]=[CH:24][N:23]=2)[CH:69]=1)[CH3:72]

Participants

7

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 53662991Methylamino-PEG3-t-butyl esterHCID 66586873HCID 66586873, compound

Product 1

HCID 66586842HCID 66586842, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-((4-(diethylamino)-2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)phenyl)carbamoyl)benzoic acid (1.81 mmol, 1.2 g), tert-butyl 5,8,11-trioxa-2-azatetradecan-14-oate (1.9 mmol, 554 mg) and DIEA (12.67 mmol, 1.64 g) in DMF (5 mL) was added HATU (2.17 mmol, 826 mg). The mixture was stirred at 60° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water (2×), sat. aqueous NaHCO3 (1×), brine (1×), dried and concentrated. The residue was purified by column to give a syrup (1.17 g, 75%).

Workup

  1. washwashed with water (2×), sat. aqueous NaHCO3 (1×), brine (1×)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column

Sources & evidence

ORD record
ord-34ffaab1352e42359b2cc653d7ddd696
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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