Trifluoroacetic acid → [7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(piperazine-1-sulfonyl)-phenyl]-amine TFA salt

HRID 273531Notes

Reaction equation

HRID 273531 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[N:25]=[N:26][C:27]4[CH:33]=[C:32]([C:34]5[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=5[Cl:41])[CH:31]=[C:30]([CH3:42])[C:28]=4[N:29]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]>C(Cl)Cl>[OH:49][C:43]([C:45]([F:48])([F:47])[F:46])=[O:44].[Cl:40][C:39]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:41])[C:34]=1[C:32]1[CH:31]=[C:30]([CH3:42])[C:28]2[N:29]=[C:24]([NH:23][C:20]3[CH:19]=[CH:18][C:17]([S:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)(=[O:16])=[O:15])=[CH:22][CH:21]=3)[N:25]=[N:26][C:27]=2[CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 116502904-{4-[7-(2,6-Dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-benzenesulfonyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86601508[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(piperazine-1-sulfonyl)-phenyl]-amine TFA saltYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{4-[7-(2,6-dichloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-benzenesulfonyl}-piperazine-1-carboxylic acid tert-butyl ester (0.0696 g, 0.111 mmol, 1 equiv) was diluted with DCM (5 mL) and treated with TFA (0.051 mL, 0.664 mmol, 6 equiv). The resulting red solution was stirred at ambient temperature for 6 hours. Additional 6 equivalents of TFA were then added and the reaction was stirred for 12 hours. The solvents were then evaporated and the resulting solids collected and dried to yield a yellow powder (0.062 g, 99% yield). MS (ESI+): m/z=528.9, LC retention time: 2.70 min. 1H NMR (DMSO-d6): δ 2.72 (s, 3H), 3.13 (m, 4H), 3.22 (m, 4H), 7.53 (m, 1H), 7.68 (d, J=8.2 Hz, 2H), 7.81 (d, J=1.6 Hz, 1H), 7.84 (d, J=8.7 Hz, 2H), 8.20 (d, J=1.7 Hz, 1H), 8.32 (d, J=8.8 Hz, 2H), 8.62 (bs, 2H), 11.53 (s, 1H).

Workup

  1. stirringthe reaction was stirred for 12 hours
  2. customThe solvents were then evaporated
  3. customthe resulting solids collected
  4. customdried

Sources & evidence

ORD record
ord-262ee76ee7934674a621c2c50fc749cf
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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