Sodium Hydroxide → Trifluoroacetic acid

HRID 1987947Notes

Reaction equation

HRID 1987947 reaction equation
C1(S(O)(=O)=[O:8])C=CC=CC=1.[C:11]([NH:14][NH2:15])(=O)[CH3:12].[F:16][C:17]([F:45])([F:44])[C:18]([N:20]1[CH:25]2[CH2:26][CH2:27][CH:21]1[CH2:22][C:23](=[C:28]1[C:41]3[CH:40]=[CH:39][C:38]([C:42]#[N:43])=[CH:37][C:36]=3[O:35][C:34]3[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:24]2)=[O:19].[OH-].[Na+]>CO>[CH3:12][C:11]1[NH:43][C:42]([C:38]2[CH:39]=[CH:40][C:41]3[C:28](=[C:23]4[CH2:22][CH:21]5[NH:20][CH:25]([CH2:26][CH2:27]5)[CH2:24]4)[C:29]4[C:34]([O:35][C:36]=3[CH:37]=2)=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:15][N:14]=1.[C:18]([OH:8])([C:17]([F:45])([F:44])[F:16])=[O:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 577253399-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carbonitrileHCID 86636508Acetic hydrazide benzenesulfonic acid

Product 2

HCID 6422Trifluoroacetic acidHCID 178433930HCID 178433930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compounds 11a (0.029 g, 0.125 mmol) and 5e (0.051g, 0.124 mmol) was exposed to microwave irradition (300 W) at 200° C. for 10 min. After cooling, MeOH (1 mL) and 1N NaOH (1 mL) were added to the reaction mixture and the mixture was stirred at rt for 30 min. The crude product was purified by reverse phase HPLC to yield compound 35 as a TFA salt. MS m/z (MH+) 371.0; 1H NMR (CH3OH-d4) δ 1.40 (d, 2H), 1.85 (m, 2H), 1.41 (s, 3H), 3.02 (m, 4H), 3.91 (m, 2H), 7.19 (m, 4H), 7.33 (d, 2H), 7.84 (d, 1H), 7.85 (s, 1H).

Workup

  1. temperatureAfter cooling
  2. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5844e01bb1154569be53d9dc0c6ea90d
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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