Triethylamine → (2S)-2-(2-(((Benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetamido)-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide

HRID 707506Notes

Reaction equation

HRID 707506 reaction equation
[NH2:1][C@@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:25][CH:24]=1)[C:3]([N:5]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=1)=[O:4].[CH2:34]([NH:41][C:42]([NH:44][N:45]([CH2:50][CH:51]=[CH2:52])[CH2:46][C:47](O)=[O:48])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[CH2:34]([NH:41][C:42]([NH:44][N:45]([CH2:50][CH:51]=[CH2:52])[CH2:46][C:47]([NH:1][C@@H:2]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[CH:27][CH:28]=1)[C:3]([N:5]([CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=1)=[O:4])=[O:48])=[O:43])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594799102-(1-Allyl-2-(benzylcarbamoyl)hydrazinyl)acetic acidHCID 118162420(2S)-2-Amino-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide

Product 1

HCID 118162464(2S)-2-(2-(((Benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetamido)-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamideYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixed solution of (2S)-2-amino-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide (881 mg, 1.91 mmol) described in Production Example 2-2 and DMF (10.0 mL) were added 2-(((benzylcarbamoyl)amino)(prop-2-en-1-yl)amino)acetic acid (503 mg, 1.91 mmol) described in International Publication No. 2009148192, triethylamine (532 μL, 3.82 mmol) and HATU (871 mg, 2.29 mmol) at room temperature. The resultant mixture was stirred at room temperature for 35 minutes. Water was added to the reaction mixture, and the resultant solution was extracted with ethyl acetate. An organic layer was washed with water and saturated brine, was then dried over anhydrous magnesium sulfate, and was then filtrated. The solvent was evaporated under a reduced pressure, the resultant residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=20:1) to give the title compound (1.22 g, yield: 91%).

Workup

  1. customat room temperature
  2. extractionthe resultant solution was extracted with ethyl acetate
  3. washAn organic layer was washed with water and saturated brine
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. filtrationwas then filtrated
  6. customThe solvent was evaporated under a reduced pressure
  7. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-2d21f382606f42008baec54438354d35
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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