HCID 58287145, compound → HCID 71811351, compound

HRID 1754416Notes

Reaction equation

HRID 1754416 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:17][CH:16]3[N:12]([C:13](=[O:18])[CH2:14][CH2:15]3)[C:11]([CH3:20])([CH3:19])[CH2:10]2)[C:5]([F:21])=[CH:4][N:3]=1.[NH2:22][C:23]1[C:24]([F:39])=[CH:25][C:26]([CH:36]2[CH2:38][CH2:37]2)=[C:27]([N:29]2[C:33](=[O:34])[N:32]([CH3:35])[N:31]=[N:30]2)[CH:28]=1>C(O)(C(F)(F)F)=O.C(O)(C)C>[F:21][C:5]1[C:6]([NH:8][CH:9]2[CH2:17][CH:16]3[N:12]([C:13](=[O:18])[CH2:14][CH2:15]3)[C:11]([CH3:20])([CH3:19])[CH2:10]2)=[N:7][C:2]([NH:22][C:23]2[C:24]([F:39])=[CH:25][C:26]([CH:36]3[CH2:38][CH2:37]3)=[C:27]([N:29]3[C:33](=[O:34])[N:32]([CH3:35])[N:31]=[N:30]3)[CH:28]=2)=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 58287145HCID 58287145, compoundHCID 86704470HCID 86704470, compound

Product 1

HCID 71811351HCID 71811351, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(2-chloro-5-fluoropyrimidin-4-ylamino)-hexahydro-5,5-dimethylindolizin-3(5H)-one isomer A (cis) (50 mg), 1-(5-amino-2-cyclopropyl-4-fluorophenyl)-4-methyl-1H-tetrazol-5(4H)-one (50 mg) and TFA (5 drops) in isopropanol (1 ml) was heated at 100° C. overnight in a sealed vial. After allowing to cool to room temperature, the solvent was removed in vacuo and the residue was purified by Combiflash chromatography (2.0 M ammonia methanol in dichloromethane=0-30%) to give product as racemic mixture.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by Combiflash chromatography (2.0 M ammonia methanol in dichloromethane=0-30%)
  4. customto give product as racemic mixture

Sources & evidence

ORD record
ord-0d43656b738b428195c5b07f8bae45cc
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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