Water → HCID 71143971, compound

HRID 2173059Notes

Reaction equation

HRID 2173059 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20](Cl)[C:19]3[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=3[C:17]=2[F:34])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:35][CH:36]([F:55])[C:37]1[CH:41]=[C:40]([Sn](CCCC)(CCCC)CCCC)[S:39][N:38]=1.O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([NH:15][C:16]2[N:21]=[C:20]([C:40]3[S:39][N:38]=[C:37]([CH:36]([F:55])[F:35])[CH:41]=3)[C:19]3[C:23](=[O:33])[N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][C:18]=3[C:17]=2[F:34])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 71143866HCID 71143866, compoundHCID 86654748tert-Butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

Product 1

HCID 71143971HCID 71143971, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 6-((3R,4R)-3-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-ylamino)-4-chloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (50 mg, 0.100 mmol), 3-(difluoromethyl)-5-(tributylstannyl)isothiazole (296 mg, 0.699 mmol) and tetrakis (triphenylphosphine)palladium(0) (57.7 mg, 0.050 mmol) in toluene (2.0 mL) was heated to 120° C. for 45 minutes via microwave irradiation. The reaction mixture was poured into water and was extracted with EtOAc. The extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (Flash 60 column) eluting with hexane/EtOAc (1:1) to yield the title compound as a mixture with byproduct. The crude product was used without further purification.

Workup

  1. extractionwas extracted with EtOAc
  2. dry with materialThe extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (Flash 60 column)
  5. washeluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-458b50f6cdb44e65b5ff937a25ae324c
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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