Hydrochloric Acid → 2-Amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester hydrochloric acid salt

HRID 1176936Notes

Reaction equation

HRID 1176936 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:20]([NH:22][O:23][CH2:24][CH2:25][O:26][C:27](=[O:33])[CH:28]([NH2:32])[CH:29]([CH3:31])[CH3:30])=[O:21])=[CH:11][C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]=2[F:19])=[C:4]([Cl:34])[CH:3]=1.Cl>CCO.CCOCC>[ClH:34].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:20]([NH:22][O:23][CH2:24][CH2:25][O:26][C:27](=[O:33])[CH:28]([NH2:32])[CH:29]([CH3:31])[CH3:30])=[O:21])=[CH:11][C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]=2[F:19])=[C:4]([Cl:34])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 724547202-amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester

Product 1

HCID 865928812-Amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester hydrochloric acid saltYield 187.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

2-Amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester (325 mg) was dissolved in about 1.5 mL of absolute EtOH, and 0.35 mL of 2N HCl in ether was added to give a thick precipitate. As additional 1.5 mL of ether were added to make the slurry thin. The slurry was mixed for 5-10 minutes and concentrated on a rotary evaporator. The damp solids were slightly yellowish and dried under high vacuum at room temperature overnight to give 0.325 g (94%) of the HCl salt. 1H NMR (400 MHz, DMSO-d6) δ: 0.97 (d, J=6.6 Hz, 3H), 1.00 (d, J=6.6 Hz, 3H), 2.20 (m br, 1H), 3.91 (s, 3H), 3.95 (s br, 1H), 4.09 (m br, 2H), 4.34 (m br, 1H), 4.43 (m br, 1H), 6.37 (dd, JH-H=8.8 Hz, JF-H=4.3 Hz virtual coupling, 1H), 7.27 (dd, J=8.8 Hz, 2.3 Hz, 1H), 7.65 (d, J=2.2 Hz, 1H), 7.78 (s, 1H), 7.92 (s, 1H), 8.37 (s br, 3H), 8.43 (s, 1H), 11.86 (s br, 1H). 19F NMR (376 MHz, DMSO-d6) δ: −132.98.

Workup

  1. customto give a thick precipitate
  2. additionThe slurry was mixed for 5-10 minutes
  3. concentrationconcentrated on a rotary evaporator
  4. customdried under high vacuum at room temperature overnight

Sources & evidence

ORD record
ord-0657e835e84a41119c75489e7cfc110e
Source dataset
uspto-grants-2010_11
Patent number
US07842816B2

Reaction notes

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