HCID 22929860, compound → HCID 22929965, compound

HRID 1295932Notes

Reaction equation

HRID 1295932 reaction equation
[CH3:1][NH:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[C:7]([CH2:12][N:13]=[N+]=[N-])=[CH:6][C:5]=1[O:16][CH2:17][CH3:18]>O1CCCC1.N.C(P(CC)CC)C>[CH3:1][NH:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][C:5]=1[O:16][CH2:17][CH3:18])[CH2:12][N:13]=[C:10]2[NH2:11])=[O:19]

Participants

5

Reactant 1

HCID 22929860HCID 22929860, compound

Product 1

HCID 22929965HCID 22929965, compoundYield 43.6%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolventHCID 27365TriethylphosphineSolvent

Conditions

Temperature
50 °C

Procedure

After dissolving N1-methyl-4-(azidomethyl)-5-cyano-2-ethoxybenzamide (931 mg) in tetrahydrofuran (10 ml), 28% aqueous ammonia (2 ml) and triethylphosphine (0.4 ml) were added in that order. The mixture was stirred at 50° C. for 15 minutes. The precipitated crystals were filtered off, washed with tetrahydrofuran, water and ethyl acetate in that order and dried to yield the title compound (365 mg).

Workup

  1. additionwere added in that order
  2. filtrationThe precipitated crystals were filtered off
  3. washwashed with tetrahydrofuran, water and ethyl acetate in that order
  4. customdried

Sources & evidence

ORD record
ord-3e5ef1b9426a41e2ad7c3258811dfae9
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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