Ammonium Hydroxide → HCID 57431655, compound

HRID 545528Notes

Reaction equation

HRID 545528 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[CH2:7][C:6]2=1)#[N:2].N[NH:31][C:32]([NH2:34])=[S:33].[NH4+].[OH-]>FC(F)(F)C(O)=O>[NH2:34][C:32]1[S:33][C:1]([C:3]2[CH:4]=[C:5]3[C:13](=[CH:14][CH:15]=2)[N:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[C:11]2[CH2:10][CH2:9][CH:8]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[CH2:7][C:6]3=2)=[N:2][N:31]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 2723789ThiosemicarbazideHCID 57431643HCID 57431643, compound

Product 1

HCID 57431655HCID 57431655, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Heat a mixture of N-[6-cyano-9-(3-fluorobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]isobutyramide (example 51) (0.500 g, 1.28 mmol) and thiosemicarbazide (0.129 g, 1.41 mmol) in trifluoroacetic acid (5 ml) at 70° C. under nitrogen for 18 h. Pour the mixture onto dilute NH4OH solution and collect 0.510 g of the resultant precipitate by filtration. Azetrope the precipitate with absolute EtOH and purify by silica chromatography eluting with 0.05% NH4OH in EtOAc to give 0.10 g of a white solid. MS (ES): m/z 464 (M+1); HPLC: Rt=1.89 min, (100%); m.p.=251-254° C.

Workup

  1. temperatureHeat
  2. customcollect 0.510 g of the resultant precipitate
  3. filtrationby filtration
  4. customAzetrope the precipitate with absolute EtOH and purify by silica chromatography
  5. washeluting with 0.05% NH4OH in EtOAc

Sources & evidence

ORD record
ord-d2b0e4a0dfa944678e9e8384c9379f93
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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