Diisopropylethylamine → HCID 66818366, compound

HRID 1755114Notes

Reaction equation

HRID 1755114 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]([O:28][CH2:29][CH2:30][N:31]([CH3:56])[C:32]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][S:42]([N:45]2[CH2:50][CH2:49][C:48]([NH2:54])([C:51]([NH2:53])=[O:52])[CH2:47][CH2:46]2)(=[O:44])=[O:43])=[C:36]([CH3:55])[CH:35]=1)=[O:33])[CH:26]=[CH2:27].[CH2:57]([O:61][C:62]1[CH:63]=[C:64]([CH:68]=[CH:69][C:70]=1[C:71]([F:74])([F:73])[F:72])[C:65](O)=[O:66])[CH2:58][CH:59]=[CH2:60].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH2:25]([O:28][CH2:29][CH2:30][N:31]([CH3:56])[C:32]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][S:42]([N:45]2[CH2:46][CH2:47][C:48]([NH:54][C:65](=[O:66])[C:64]3[CH:68]=[CH:69][C:70]([C:71]([F:73])([F:74])[F:72])=[C:62]([O:61][CH2:57][CH2:58][CH:59]=[CH2:60])[CH:63]=3)([C:51]([NH2:53])=[O:52])[CH2:49][CH2:50]2)(=[O:44])=[O:43])=[C:36]([CH3:55])[CH:35]=1)=[O:33])[CH:26]=[CH2:27]

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 66817527HCID 66817527, compoundHCID 66817761HCID 66817761, compound

Product 1

HCID 66818366HCID 66818366, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HATU (245 mg, 0.644 mmol) was added to a solution of 1-(2-{4-[(2-allyloxy-ethyl)-methyl-carbamoyl]-2-methyl-phenyl}-ethanesulfonyl)-4-amino-piperidine-4-carboxylic amide (250 mg), 3-but-3-enyloxy-4-trifluoromethyl-benzoic acid (155 mg, 0.596 mmol) and diisopropylethylamine (0.140 ml, 0.812 mmol) in DMF (5 ml), and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1-(2-{4-[(2-allyloxy-ethyl)-methyl-carbamoyl]-2-methyl-phenyl}-ethanesulfonyl)-4-(3-but-3-enyloxy-4-trifluoromethyl-benzoylamino)-piperidine-4-carboxylic amide as a crude compound (381 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-010ed8f1a15f4c0da74a16720087fc3e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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