Ammonia → HCID 136501883, compound

HRID 706791Notes

Reaction equation

HRID 706791 reaction equation
O[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:16][C:15](=[O:17])[C:14]3=[CH:18][CH:19]=[CH:20][N:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[N-:21]=[N+:22]=[N-:23].[Na+].FC(F)(F)C(O)=O.N>ClCCl.O>[N:21]([C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:16][C:15](=[O:17])[C:14]3=[CH:18][CH:19]=[CH:20][N:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3])=[N+:22]=[N-:23]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 136262675HCID 136262675, compound

Product 1

HCID 136501883HCID 136501883, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (135 mg, 0.50 mmol) and sodium azide (71.5 mg, 1.1 mmol) in dichloromethane (1 ml) is added a solution of trifluoroacetic acid (316 μl, 4.1 mmol) in dichloromethane (0.6 ml) dropwise under external cooling with ice. The reaction mixture is stirred for 3 days at room temperature. Water (5 ml) 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 2-[4-(1-azido-1-methyl-ethyl)-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one as white solid; HPLC/MS 1.98 min (C), [M+H] 295.

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-c0c5ab4457144fb29956af47365598dd
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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