Benzylamine → HCID 22097092, compound

HRID 861535Notes

Reaction equation

HRID 861535 reaction equation
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:22]([F:25])([F:24])[F:23])=[C:12]([N:15]3[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]3[CH3:21])[CH:13]=2)[NH:8][C:7](=[O:26])[C:6]1=[O:27])(O)=[O:2].[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.O>[CH2:28]([NH:35][C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:22]([F:23])([F:25])[F:24])=[C:12]([N:15]3[C:16]([CH3:21])=[CH:17][CH:18]=[C:19]3[CH3:20])[CH:13]=2)[NH:8][C:7](=[O:26])[C:6]1=[O:27])=[O:2])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22097151HCID 22097151, compound

Product 1

HCID 22097092HCID 22097092, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

1.6 g (4.2 mmol) of the compound of Example 72 and 0.5 ml (4.6 mmol) of benzylamine were dissolved in 50 ml of anhydrous dimethylformamide under a nitrogen atmosphere. At 0° C., 1 ml (4.6 mmol) of diphenylphosphoryl azide dissolved in 10 ml of anhydrous dimethylformamide, and 1.3 ml (9.2 mmol) of triethylamine were successively added dropwise. The mixture was then stirred at room temperature for 16 h and subsequently diluted with water, acidified and extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was recrystallized from ethanol to yield 1.1 g (56%) of the product. Melting point>250° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-20737fd52c9b45a3a8b2bccf75068a96
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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