Hydrochloric Acid → 2-[(Aminocarbonyl)amino]-N-[(3S)-azepan-3-yl]-5-(4-methoxyphenyl)thiophene-3-carboxamide

HRID 30339Notes

Reaction equation

HRID 30339 reaction equation
Cl.[NH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:9][C:10]=1[C:11]([NH:13][C@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1)=[O:12])=[O:4]>O1CCOCC1>[NH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)=[CH:9][C:10]=1[C:11]([NH:13][C@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1)=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 69271799tert-Butyl (3S)-3-({[2-[(aminocarbonyl)amino]-5-(4-methoxyphenyl)-3-thienyl]carbonyl}amino)azepane-1-carboxylate

Product 1

HCID 116034702-[(Aminocarbonyl)amino]-N-[(3S)-azepan-3-yl]-5-(4-methoxyphenyl)thiophene-3-carboxamideYield 64.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

hydrochloride. To a stirred solution of tert-butyl(3S)-3-({[2-[(aminocarbonyl)amino]-5-(4-methoxyphenyl)-3-thienyl]carbonyl}amino)azepane-1-carboxylate (0.9 g, 1.8 mmol) in 1,4-dioxane (10 mL) was added 4.0N HCl in 1,4-dioxane (10 mL, 40 mmol). A precipitate forms shortly and the reaction is stirred for an additional 4 h at room temperature. Due to the hygroscopic nature of the salt form, the solvent was removed under vacuum. The residue was dissolved in methanol and concentrated under vacuum (2×) to yield and off-white solid. Recrystallization from using 2-propanol gave 0.45 g (59%) of a white solid. 1H NMR (d6-DMSO, δ 10.9, s, 1H; δ 9.58, br s, 1H; δ 9.29, br s, 1H; δ 8.39, d, 1H; δ 7.82, s, 1H; δ 7.48, d, 2H; δ 6.96, d, 2H; δ 4.36, m, 1H; δ 3.77, s, 3H; δ 3.29, m, 1H; δ 3.20, m, 2H; δ 3.07, m, 1H; δ 1.98, m, 1H; δ 1.84, m, 4H; δ 1.59, m, 1H), LC/MS (APCI, ES, M+H=389).

Workup

  1. customDue to the hygroscopic nature of the salt form, the solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in methanol
  3. concentrationconcentrated under vacuum (2×)
  4. customto yield
  5. customRecrystallization

Sources & evidence

ORD record
ord-9383c7fbb1f74eff999ca589773be6a7
Source dataset
uspto-grants-2008_09
Patent number
US07423061B2

Reaction notes

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