Trifluoroacetic acid → (2-ethanesulfonyl-ethyl)-methyl-(3H-3,4,8a-triaza-as-indacen-8-yl)-amine

HRID 1808694Notes

Reaction equation

HRID 1808694 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][N:8]([CH3:29])[C:9]1[N:20]2[C:12]([CH:13]=[N:14][C:15]3[N:16](COCC[Si](C)(C)C)[CH:17]=[CH:18][C:19]=32)=[CH:11][CH:10]=1)(=[O:5])=[O:4])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([S:3]([CH2:6][CH2:7][N:8]([CH3:29])[C:9]1[N:20]2[C:12]([CH:13]=[N:14][C:15]3[NH:16][CH:17]=[CH:18][C:19]=32)=[CH:11][CH:10]=1)(=[O:4])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66838847(2-ethanesulfonyl-ethyl)-methyl-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-3,4,8a-triaza-as-indacen-8-yl]-amine

Product 1

HCID 66839155(2-ethanesulfonyl-ethyl)-methyl-(3H-3,4,8a-triaza-as-indacen-8-yl)-amineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Ethanesulfonyl-ethyl)-methyl-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-3,4,8a-triaza-as-indacen-8-yl]-amine (68 mg, 0.16 mmol) was taken up in methylene chloride (3 mL) and TFA (2 mL) and lightly capped and stirred for 2 hours. The volatiles were removed on the rotovap and the remainder was taken up in CH2C12 (25 mL). The volatiles were stripped and the remainder placed on a drying pump for 30 minutes. The material was taken up methylene chloride (2 mL) and ethylene diamine (2 mL) and stirred for 1.5 hours. Ethyl acetate (40 ml) and brine (40 mL) was added and the material shaken in a separatory funnel. The ethyl acetate phase was collected and washed with an equal volume of brine solution. The aqueous phases were back extracted with ethyl acetate (2×30 ml), the organics combined, dried (MgSO4), filtered and stripped. The crude was purified via preparative TLC using 7% MeOH in CH2Cl2 as eluant to provide 49 mg of (2-ethanesulfonyl-ethyl)-methyl-(3H-3,4,8a-triaza-as-indacen-8-yl)-amine as a green-black crystalline solid. MS (M+H)+=291.

Workup

  1. customThe volatiles were removed on the rotovap
  2. waitthe remainder placed on a drying pump for 30 minutes
  3. stirringstirred for 1.5 hours
  4. additionEthyl acetate (40 ml) and brine (40 mL) was added
  5. stirringthe material shaken in a separatory funnel
  6. customThe ethyl acetate phase was collected
  7. washwashed with an equal volume of brine solution
  8. extractionThe aqueous phases were back extracted with ethyl acetate (2×30 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customThe crude was purified via preparative TLC

Sources & evidence

ORD record
ord-84033ab70f284710bd301861877f0935
Source dataset
uspto-grants-2013_01
Patent number
US08361962B2

Reaction notes

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