Diphenyl N-Cyanocarbonimidate → HCID 178490150, compound

HRID 431070Notes

Reaction equation

HRID 431070 reaction equation
[CH:1]1([O:6][C:7]2[N:12]=[C:11]([CH:13]([CH3:16])[CH2:14][NH2:15])[CH:10]=[CH:9][C:8]=2[O:17][CH3:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:19]1[CH:24]=[CH:23][C:22]([O:25][C:26](OC2C=CC=CC=2)=[N:27][C:28]#[N:29])=[CH:21][CH:20]=1>C(O)C>[C:28]([N:27]=[C:26]([O:25][C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1)[NH:15][CH2:14][CH:13]([C:11]1[CH:10]=[CH:9][C:8]([O:17][CH3:18])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[N:12]=1)[CH3:16])#[N:29]

Participants

4

Reactant 2

HCID 688090Diphenyl N-CyanocarbonimidateHCID 18763378HCID 18763378, compound

Product 1

HCID 178490150HCID 178490150, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-6-(cyclopentyloxy)-5-methoxy-β-methyl-2-pyridineethanamine (0.037 mol) and diphenyl N-cyanocarbonimidate (0.037 mol) in ethanol (100 ml) was stirred for one day at RT. The precipitate was filtered off, washed with ethanol, DIPE, then dried, yielding 9 g (61.7%) of (±)-phenyl N′-cyano-N-[2-[6-(cyclopentyloxy)-5-methoxy-2-pyridinyl]propyl]carbamimidate(interm. 9). The filtrate was evaporated under reduced pressure. The residue was dissolved in CH2Cl2. The organic solution was washed three times with 2 N NaOH. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 4.1 g of intermediate (9). Total yield is 89%.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethanol, DIPE
  3. customdried

Sources & evidence

ORD record
ord-5225fd747eb345e892d1d16dbfcb8165
Source dataset
uspto-grants-2003_12
Patent number
US06656959B1

Reaction notes

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