Dichloromethane ethanol → HCID 6481660, compound

HRID 606325Notes

Reaction equation

HRID 606325 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[CH:22]=[CH:21][C:20]([O:23][C:24]5[CH:29]=[CH:28][C:27]([NH:30]C(OC(C)(C)C)=O)=[CH:26][CH:25]=5)=[CH:19][N:18]=4)=[O:15])[C@H:7]3[C:6]=2[C:5]([F:38])=[CH:4][CH:3]=1.Cl.CC(O)=O.CCO.C(Cl)Cl>C(Cl)Cl>[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:22]=[CH:21][C:20]([O:23][C:24]5[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=5)=[CH:19][N:18]=4)=[O:15])[C@H:7]3[C:6]=2[C:5]([F:38])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21584144Dichloromethane ethanolHCID 22641269Acetate-hydrochloric acidHCID 59687010HCID 59687010, compound

Product 1

HCID 6481660HCID 6481660, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dried N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N′-[5-(4-(N-t-butoxycarbonylamino)phenoxy)-2-pyridinyl]urea (242 mg, 0.46 mmol) was dissolved in methylene chloride (2 ml) and then 1M HCl/AcOH (4.6 ml) was added and the reaction solution was stirred for 60 minutes at room temperature. The volatile matters were removed by evaporation. The residue was worked up by extractions between methylene chloride and sat. aq. NaHCO3. The organic phase was dried through sodium sulfate and evaporated. Silica gel column chromatography (1-3% EtOH/methylene chloride gradient) gave 139 mg of pure product as white powder (71% yield).

Workup

  1. customThe volatile matters were removed by evaporation
  2. extractionThe residue was worked up by extractions between methylene chloride and sat. aq. NaHCO3
  3. dry with materialThe organic phase was dried through sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-e88f969e163e449c993f629ad20c25b3
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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