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

HRID 30336Notes

Reaction equation

HRID 30336 reaction equation
Cl.[NH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:9][C:10]=1[C:11]([NH:13][C@H:14]1[CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1)=[O:12])=[O:4]>CO.O1CCOCC1>[NH2:2][C:3]([NH:5][C:6]1[S:7][C:8]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)=[CH:9][C:10]=1[C:11]([NH:13][C@H:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1)=[O:12])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 69271788tert-Butyl(3S)-3-({[2-[(aminocarbonyl)amino]-5-(4-methoxyphenyl)-3-thienyl]carbonyl}amino)piperidine-1-carboxylate

Product 1

HCID 115090482-[(Aminocarbonyl)amino]-5-(4-methoxyphenyl)-N-[(3S)-piperidin-3-yl]thiophene-3-carboxamideYield 92.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

hydrochloride. To a stirred solution of tert-butyl(3S)-3-({[2-[(aminocarbonyl)amino]-5-(4-methoxyphenyl)-3-thienyl]carbonyl}amino)piperidine-1-carboxylate (0.70 g, 1.47 mmol) in anhydrous MeOH (5.0 mL) was added 4.0N HCl in 1,4-dioxane (10 mL). A small amount of precipitate forms shortly and the reaction is stirred for an additional 4 h at room temperature. The solvent was removed under vacuum. The residue was redissolved in methanol and concentrated under vacuum (2×) to yield 0.51 g (85%) of a light yellow solid. 1H NMR (d6-DMSO δ 10.9, s, 1H; δ 9.39, br s, 1H; δ 9.20, br s, 1H; δ 8.37, d, 1H; δ 7.88, s, 1H; δ 7.49, d, 2H; δ 6.96, d, 2H; δ 6.97, br s, 2H; δ 4.24, m, 1H; δ 3.77, s, 3H; δ 3.29, m, 1H; δ 3.11, m, 1H; δ 2.93, m, 2H; δ 1.91, m, 2H; δ 1.68, m, 2H), LC/MS (APCI, ES, M+H=6875).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionThe residue was redissolved in methanol
  3. concentrationconcentrated under vacuum (2×)

Sources & evidence

ORD record
ord-4424931cc2734e1cb093bf5b771d336f
Source dataset
uspto-grants-2008_09
Patent number
US07423061B2

Reaction notes

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