Guanidine → HCID 18945134, compound

HRID 399866Notes

Reaction equation

HRID 399866 reaction equation
[C:1]([C:4]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10]3=[CH:16][CH:17]=[CH:18][N:9]3[C:8]=2[CH:7]=[C:6]([Cl:19])[CH:5]=1)(O)=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:35][C:36]([NH2:38])=[NH:37]>O1CCCC1.N1C=CC=CC=1.O.C(OCC)(=O)C>[ClH:19].[Cl:19][C:6]1[CH:5]=[C:4]([C:1]([N:35]=[C:36]([NH2:38])[NH2:37])=[O:2])[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[C:10]3=[CH:16][CH:17]=[CH:18][N:9]3[C:8]=2[CH:7]=1

Participants

9

Reactant 4

HCID 3520GuanidineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 10356172HCID 10356172, compound

Product 1

HCID 18945134HCID 18945134, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-carboxy-8-chloro-4,4-dimethyl-4H-pyrrolo[2,1-c][1,4]benzoxazine (0.7 g) and triethylamine (0.39 ml) in tetrahydrofuran (7 ml) and pyridine (14 ml) was added isobutyl chloroformate (0.38 g) under ice cooling. After being stirred for 2 hours at 7°-10° C., guanidine (0.3 g) was added to the reaction mixture and the whole was stirred for 8 hours at room temperature. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (100 ml). The organic layer was washed successively with 10% potassium carbonate aqueous solution, brine, dried over magnesium sulfate and evaporated in vacuo. The residue was treated with hydrogen chloride-ethanol to afford 8-chloro-4,4-dimethyl-6-diaminomethyleneaminocarbonyl-4H-pyrrolo[2,1-c][1,4]benzoxazine hydrochloride

Workup

  1. stirringthe whole was stirred for 8 hours at room temperature
  2. washThe organic layer was washed successively with 10% potassium carbonate aqueous solution, brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. additionThe residue was treated with hydrogen chloride-ethanol

Sources & evidence

ORD record
ord-e1521ac075604ac4967681d077c7955f
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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