HCID 14115670, compound → HCID 178437163, compound

HRID 1976113Notes

Reaction equation

HRID 1976113 reaction equation
[CH2:1]([O:8][C:9]([N:11]=[C:12]([NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[NH:13][C:14]1[C:23]([CH3:24])=[C:22]2[C:17]([CH:18]=[CH:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C:37]1C(C)=C2C(C=CC=N2)=CC=1.C(N=C(S)N(C(OCC1C=CC=CC=1)=O)C(OCC1C=CC=CC=1)=O)C>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]=[C:12]([NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[NH:13][C:14]1[C:23]([CH2:24][CH3:37])=[C:22]2[C:17]([CH:18]=[CH:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14115670HCID 14115670, compoundHCID 178430658HCID 178430658, compoundHCID 178465517HCID 178465517, compound

Product 1

HCID 178437163HCID 178437163, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-[N2,N3-Bis(benzyloxycarbonyl)guanidino]-8-methylquinoline. To a pale yellow solution of 500 mg of 7-amino-8-methylquinoline in 20 mL of tetrahydrofuran are added 1.18 g of ethyl N,N-bis(benzyloxy-carbonyl)pseudothiourea and 1.01 g of mercuric acetate and the mixture is stirred at room temperature for 1 hour. The suspension is diluted with ethyl acetate and the organic layer is washed with water followed by brine. The aqueous layers are extracted with ethyl acetate; the combined organic layers are dried over magnesium sulfate, filtered and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 50% ethyl acetate/hexanes and recrystallization from hexanes/methylene chloride to provide 1.257 g of 7-[N2,N3-bis(benzyloxycarbonyl)guanidino]-8-ethylquinoline as a white solid.

Workup

  1. washthe organic layer is washed with water
  2. extractionThe aqueous layers are extracted with ethyl acetate
  3. dry with materialthe combined organic layers are dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe residue is purified by flash column chromatography on silica gel
  6. washeluting with 50% ethyl acetate/hexanes and recrystallization from hexanes/methylene chloride

Sources & evidence

ORD record
ord-657acd9daa804767863a5934dd8ca44e
Source dataset
uspto-grants-2001_05
Patent number
US06225331B1

Reaction notes

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