HCID 67047981, compound → HCID 67047754, compound

HRID 606330Notes

Reaction equation

HRID 606330 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@@H:8]3[C@@H:12]([NH:13][C:14]([NH:16][C:17]4[N:22]=[CH:21][C:20]([O:23][C:24]5[CH:40]=[CH:39][C:27]([C:28]([NH:30][NH:31]C(OC(C)(C)C)=O)=[O:29])=[CH:26][CH:25]=5)=[CH:19][CH:18]=4)=[O:15])[C@@H:7]3[C:6]=2[C:5]([F:41])=[CH:4][CH:3]=1>ClCCl>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@@H:8]3[C@@H:12]([NH:13][C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([O:23][C:24]5[CH:40]=[CH:39][C:27]([C:28]([NH:30][NH2:31])=[O:29])=[CH:26][CH:25]=5)=[CH:21][N:22]=4)=[O:15])[C@@H:7]3[C:6]=2[C:5]([F:41])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67047981HCID 67047981, compound

Product 1

HCID 67047754HCID 67047754, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The tert-butyl 2-[4-({6-[({[(1S,1aS,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]amino}carbonyl)amino]-3-pyridinyl}oxy)benzoyl]hydrazine carboxylate (49 mg, 0.089 mmol) in a mixture of dichloromethane (0.5 mL) and trifluoroacetic (0.5 mL) was stirred at room temperature for 30 min. The reaction was concentrated and purified on column chromatography (silica gel, 2% MeOH in CH2Cl2) to give the compound N-[(1S,1aS,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N′-{5-[4-(hydrazinocarbonyl)phenoxy]-2-pyridinyl}urea (17.6 mg, yield: 42%).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified on column chromatography (silica gel, 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f06cf6200ebf4b299dacfb18df6415ed
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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