Ammonia → HCID 89826370, compound

HRID 2272979Notes

Reaction equation

HRID 2272979 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17](O)([CH3:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:6][N:5]2[CH:21]=1.[N-:22]=[N+:23]=[N-:24].[Na+].FC(F)(F)C(O)=O.N>ClCCl.C1CCCCC1.C(OCC)(=O)C>[N:22]([C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:7]2[NH:8][C:9](=[O:10])[C:4]3[N:5]([CH:21]=[C:2]([F:1])[CH:3]=3)[CH:6]=2)=[CH:12][CH:13]=1)([CH3:19])[CH3:18])=[N+:23]=[N-:24]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 71765087HCID 71765087, compound

Product 1

HCID 89826370HCID 89826370, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21867204Cyclohexane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 143 mg (0.5 mmol) 7-fluoro-3-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-pyrrolo[1,2-a]pyrazin-1-one and 71.5 mg (1.1 mmol) sodium azide in 1 ml dichloromethane is added dropwise under external cooling with ice a solution of 316 μl (4.1 mmol) trifluoroacetic acid in 0.6 ml dichloromethane. The reaction mixture is stirred for 3 hours at 0° C. Ice and 25% aqueous ammonia are added to obtain a two-phase mixture with a pH of 11. Then a 1:1 mixture of cyclohexane/ethyl acetate is added. The organic phase is separated, dried over sodium sulfate and evaporated to afford 3-[4-(1-azido-1-methyl-ethyl)-phenyl]-7-fluoro-2H-pyrrolo[1,2-a]pyrazin-1-one as beige powder; HPLC/MS 2.29 min (A), [M+H] 312.

Workup

  1. additionis added dropwise
  2. customto obtain a two-phase mixture with a pH of 11
  3. additionis added
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-5dd3f5110b57491ca70a0386b3239c62
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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