Ammonia → HCID 90040127, compound

HRID 2207334Notes

Reaction equation

HRID 2207334 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][C:16]([C:19](O)([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].FC(F)(F)C(O)=O.N>ClCCl.O>[N:23]([C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:7]2[NH:8][C:9](=[O:12])[C:10]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=3)=[CH:14][CH:15]=1)([CH3:21])[CH3:20])=[N+:24]=[N-:25]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 73057456HCID 73057456, compound

Product 1

HCID 90040127HCID 90040127, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 7-fluoro-3-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-isoquinolin-1-one (149 mg, 0.50 mmol) and sodium azide (71.5 mg, 1.10 mmol) in dichloromethane (1 ml) is added a solution of trifluoroacetic acid (316 μl, 4.1 mmol) in dichloromethane (0.5 ml) dropwise under external cooling with ice. The reaction mixture is stirred for 2 hours at room temperature. Water and 25% aqueous ammonia (0.5 ml) are added. The organic phase is separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over sodium sulfate and evaporated to afford 3-[4-(1-azido-1-methyl-ethyl)-phenyl]-7-fluoro-2H-isoquinolin-1-one as white powder; HPLC/MS 2.07 min (A), [M+H] 323.

Workup

  1. temperatureunder external cooling with ice
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-6b0e011df8364c59972b15063c81feec
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

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