Isopropylamine → HCID 59208314, compound

HRID 2061871Notes

Reaction equation

HRID 2061871 reaction equation
[Br:1][C:2]1[C:3]([C:16]2[S:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=2)=[CH:4][C:5]([NH:8][C:9](=[O:15])OC(C)(C)C)=[N:6][CH:7]=1.[CH:25]([NH2:28])([CH3:27])[CH3:26]>C(#N)C>[Br:1][C:2]1[C:3]([C:16]2[S:17][CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[N:20]=2)=[CH:4][C:5]([NH:8][C:9]([NH:28][CH:25]([CH3:27])[CH3:26])=[O:15])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 67028693HCID 67028693, compound2×

Product 1

HCID 59208314HCID 59208314, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of tert-butyl 5-bromo-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-2-ylcarbamate (Intermediate 87, 25 g, 59 mmol), isopropyl amine (250 mL) and acetonitrile (100 mL) was heated at 130° C. in a Parr Bomb apparatus for 50 h (˜150 PSI). The reaction mixture was cooled to room temperature and the reaction filtered through Celite, and the filtrate was washed with tetrahydrofuran (˜300 mL). The solvents were evaporated and the residue was triturated with methanol (200 mL), filtered and the solid was dried to give 14.6 g of product.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe reaction filtered through Celite
  3. washthe filtrate was washed with tetrahydrofuran (˜300 mL)
  4. customThe solvents were evaporated
  5. customthe residue was triturated with methanol (200 mL)
  6. filtrationfiltered
  7. customthe solid was dried

Sources & evidence

ORD record
ord-08e81bdbe5d44de1afb809ee04029684
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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