Trifluoroacetic acid → HCID 136358497, compound

HRID 601358Notes

Reaction equation

HRID 601358 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH2:21][C:22]1[CH:50]=[CH:49][C:25]2[NH:26][C:27]([C:32]3[C:33](=[O:48])[N:34]([CH2:43][CH2:44][CH:45]([CH3:47])[CH3:46])[C:35]4[C:40]([C:41]=3[OH:42])=[CH:39][CH:38]=[CH:37][N:36]=4)=[N:28][S:29](=[O:31])(=[O:30])[C:24]=2[CH:23]=1.[N+:51]([O-])([O-:53])=[O:52].[K+]>>[F:1][C:2]([F:7])([F:6])[C:3]([NH:21][C:22]1[CH:50]=[CH:49][C:25]2[NH:26][C:27]([C:32]3[C:33](=[O:48])[N:34]([CH2:43][CH2:44][CH:45]([CH3:47])[CH3:46])[C:35]4[C:40]([C:41]=3[OH:42])=[CH:39][CH:38]=[CH:37][N:36]=4)=[N:28][S:29](=[O:31])(=[O:30])[C:24]=2[C:23]=1[N+:51]([O-:53])=[O:52])=[O:4]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 24434Potassium NitrateHCID 1354307103-(7-Amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-(3-methylbutyl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 136358497HCID 136358497, compoundYield 94%

Conditions

Temperature
0 °C

Procedure

To a solution of trifluoroacetic acid (2.5 mL) and trifluoroacetic anhydride (2.5 mL) at 0° C. was added portion wise the product of Example 205 (0.5 g, 1.17 mmol). The resulting red solution was stirred at 0° C. for 30 minutes, cooled to −20° C. and treated portion wise with potassium nitrate (0.13 g, 1.3 mmol). The mixture was stirred at −20° C. for 1 hour, poured onto ice and the resulting tan solid was collected by filtration, washed with water and dried to constant mass to give the title compound (0.628 g, 94% yield). MS (ESI−) m/z 567 (M−H)−. The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) δ 0.96 (d, J=6.62 Hz, 6 H) 1.49 (m, 2 H) 1.64 (m, 1 H) 4.30 (m, 2 H) 7.16 (dd, J=7.72, 4.78 Hz, 1 H) 7.67 (m, 2 H) 8.38 (dd, J=7.54, 2.02 Hz, 1 H) 8.57 (dd, J=4.41, 1.84 Hz, 1 H) 11.61 (s, 1 H) 16.67 (s, 1 H).

Workup

  1. temperaturecooled to −20° C.
  2. stirringThe mixture was stirred at −20° C. for 1 hour
  3. additionpoured onto ice
  4. filtrationthe resulting tan solid was collected by filtration
  5. washwashed with water
  6. customdried to constant mass

Sources & evidence

ORD record
ord-f049e7b6128f49689387571edc1d0126
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

Loading…