Hydrogen Bromide → HCID 86659016, compound

HRID 1942720Notes

Reaction equation

HRID 1942720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:31][CH3:32])=[C:19]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]4)[CH:20]=[CH:21][CH:22]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C1COCC1.O.[BrH:39]>C(#N)C>[Br-:39].[C:28]([CH:26]1[CH2:27][NH+:24]([CH2:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:15]3[S:16][C:12]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[C:2]([Cl:1])[CH:3]=4)=[N:13][N:14]=3)[C:18]=2[CH2:31][CH3:32])[CH2:25]1)([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 8028TetrahydrofuranHCID 584940121-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

Product 1

HCID 86659016HCID 86659016, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylic acid (50 mg, 0.106 mmol) was added to a mixture of THF (2 mL), water (0.6 mL) and ACN (1 mL), a suspension was obtained to which was added HBr solution (0.016 mL, 40%, wt). A clear solution was obtained and stirred for 30 min at rt. Solvent was removed under the reduced pressure and dried in vacuum to give 3-carboxy-1-(3-(5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidin-1-ium bromide (56 mg) as pale yellow solid. δH (DMSO-d6, 600 MHz): 1.08 (3H, t), 1.35 (6H, m), 2.92 (2H, m), 3.67 (1H, m), 4.34 (4H, m), 4.61 (2H, m), 4.85 (1H, dt), 7.39 (1H, d), 7.48 (1H, m), 7.64 (2H, m), 7.97 (1H, d), 8.10 (1H, d), 10.25 (1H, s), 13.17 (1H, d).

Workup

  1. customa suspension was obtained to which
  2. customA clear solution was obtained
  3. customSolvent was removed under the reduced pressure
  4. customdried in vacuum

Sources & evidence

ORD record
ord-85d8343f18eb4a74a6bfb428b7763c7c
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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