Triphosgene → HCID 58902371, compound

HRID 1640219Notes

Reaction equation

HRID 1640219 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[C:18]([O:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][CH:27]([C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:35]=4)=[O:32])[CH2:28]3)=[CH:23][CH:22]=2)[CH:17]=[CH:16][N:15]=1>C1COCC1>[C:40]([C:36]1[CH:35]=[C:34]([NH:33][C:31]([CH:27]2[CH2:26][CH2:25][C:24]3[C:29](=[CH:30][C:21]([O:20][C:18]4[CH:17]=[CH:16][N:15]=[C:14]([N:13]=[C:2]=[O:4])[CH:19]=4)=[CH:22][CH:23]=3)[CH2:28]2)=[O:32])[CH:39]=[CH:38][CH:37]=1)([CH3:43])([CH3:42])[CH3:41]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 58902256HCID 58902256, compound

Product 1

HCID 58902371HCID 58902371, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of triphosgene (304 mg, 1.02 mmol) in THF (15 mL) was cooled to 0° C. To this solution was added TEA (0.74 mL, 5.32 mmol). A solution of 7-[(2-aminopyridin-4-yl)oxy]-N-(3-tert-butylphenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide (850 mg, 2.04 mmol) in THF (6 mL) was added dropwise to the reaction mixture over the 20 min. The reaction mixture was allowed to stir at 0° C. and then to warm to rt and stir for 1 h. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography to give N-(3-tert-butylphenyl)-7-[(2-isocyanatopyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxamide (510 mg, 56%) as yellow solid. LCMS: (FA) ES+442.5.

Workup

  1. temperatureto warm to rt
  2. stirringstir for 1 h
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7855b6f5152f492dab22e5f9a447203e
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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