Diisopropylethylamine → (E)-(4-(4-((1-(3-(3,5-Dichlorophenyl)acryloyl)piperidin-4-yl)amino)-4-oxobutyl)-1H-1,2,3-triazol-1-yl)methyl pivalate

HRID 1480443Notes

Reaction equation

HRID 1480443 reaction equation
[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17](=[O:25])[NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:26][C:27]1[CH:28]=[C:29](/[CH:34]=[CH:35]/[C:36](O)=[O:37])[CH:30]=[C:31]([Cl:33])[CH:32]=1.CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C.CCOC(C)=O>[C:1]([O:7][CH2:8][N:9]1[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][C:17]([NH:18][CH:19]2[CH2:20][CH2:21][N:22]([C:36](=[O:37])/[CH:35]=[CH:34]/[C:29]3[CH:28]=[C:27]([Cl:26])[CH:32]=[C:31]([Cl:33])[CH:30]=3)[CH2:23][CH2:24]2)=[O:25])[N:11]=[N:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 64421483-(3,5-Dichlorophenyl)acrylic acidHCID 86722666HCID 86722666, compound

Product 1

HCID 86722670(E)-(4-(4-((1-(3-(3,5-Dichlorophenyl)acryloyl)piperidin-4-yl)amino)-4-oxobutyl)-1H-1,2,3-triazol-1-yl)methyl pivalate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of (4-(4-oxo-4-(piperidin-4-ylamino)butyl)-1H-1,2,3-triazol-1-yl)methyl pivalate (Example 37, step 5)(200 mg, 0.516 mmol) and (E)-3-(3,5-dichlorophenyl)acrylic acid (Example 30, step 2) (112 mg, 0.516 mmol) in DMF (2 mL) at RT was added Huenig's base (0.450 mL, 2.58 mmol) followed by T3P® 50% in DMF (0.602 mL, 1.031 mmol) after a few minutes. The reaction mixture was stirred at RT for 20 hours. The reaction mixture was diluted with EtOAc and washed with a saturated solution of brine, organics dried over MgSO4, filtered, and concentrated under reduced pressure to afford the title crude product;

Workup

  1. washwashed with a saturated solution of brine
  2. dry with materialorganics dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ec6b3303712447a9c4770fb51f9771c
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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