Diisopropylethylamine → HCID 69173221, compound

HRID 2114834Notes

Reaction equation

HRID 2114834 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:20](O)=[O:21])=[CH:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:27][NH2:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([C:20]([NH:28][CH2:27][C:26]2[CH:29]=[CH:30][C:31]([F:32])=[C:24]([Cl:23])[CH:25]=2)=[O:21])=[CH:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1445393-Chloro-4-fluorobenzylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69320584HCID 69320584, compound

Product 1

HCID 69173221HCID 69173221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylic acid (200 mg, 0.67 mmol), 3-chloro-4-fluorobenzylamine (0.16 g, 1.00 mol), and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophophate (BOP, 0.35 g, 0.79 mmol) in anhydrous dichloromethane (10 mL), diisopropylethylamine (0.17 g, 1.33 mmol) was added. The resultant solution was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum, and the residue partitioned between dichloromethane and aq HCl. The organic extract was washed with aq sodium bicarbonate, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the titled amide.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue partitioned between dichloromethane and aq HCl
  4. extractionThe organic extract
  5. washwas washed with aq sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9633f726716840f5aa03ccf324de0a0d
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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