Hydrochloric Acid → N-[(3S)-Azepan-3-yl]-5-(4-methoxyphenyl)-2-{[(pyrazin-2-ylamino)carbonyl]amino}thiophene-3-carboxamide

HRID 30343Notes

Reaction equation

HRID 30343 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([NH:15][C:16]([NH:18][C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)=[O:17])=[C:12]([C:25]([NH:27][C@H:28]3[CH2:34][CH2:33][CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]3)=[O:26])[CH:11]=2)=[CH:6][CH:5]=1>CO.O1CCOCC1>[NH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][C@H:28]([NH:27][C:25]([C:12]2[CH:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[S:14][C:13]=2[NH:15][C:16]([NH:18][C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)=[O:17])=[O:26])[CH2:29]1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 69274051tert-butyl(3S)-3-{[(5-(4-methoxyphenyl)-2-{[(pyrazin-2-ylamino)carbonyl]amino}-3-thienyl)carbonyl]amino}azepane-1-carboxylate

Product 1

HCID 59789491N-[(3S)-Azepan-3-yl]-5-(4-methoxyphenyl)-2-{[(pyrazin-2-ylamino)carbonyl]amino}thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

hydrochloride. To a stirred solution of tert-butyl(3S)-3-{[(5-(4-methoxyphenyl)-2-{[(pyrazin-2-ylamino)carbonyl]amino}-3-thienyl)carbonyl]amino}azepane-1-carboxylate (0.51 g, 0.9 mmol) in 10 mL of MeOH is added 10 mL (40 mmol) of 4.0 N HCl in dioxane. The solution was stirred at room temperature for 4 h and then concentrated under vacuum. The residue was partially recrystallized by triturating in refluxing 2-propanol to yield the title compound are a light orange solid (0.30 g, 67%). 1H NMR (d6-DMSO δ 12.6, br s, 1H; δ 10.9, s, 1H; δ 9.55, br s, 1H; δ 9.24, br s, 1H; δ 8.88, s, 1H; δ 8.49, d, 1H; δ 8.35, dd, 1H; δ 8.29, d, 1H; δ 7.92, s, 1H; δ 7.54, d, 2H; δ 6.99, d, 2H; δ 4.42, m, 1H; δ 3.33, m, 1H; δ 3.23, m, 2H; δ 3.10, m, 1H; δ 2.02, m, 1H; δ 1.85, m, 4H; δ 1.62, m, 1H;), LC/MS (APCI, ES, M+H=467).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was partially recrystallized
  3. customby triturating
  4. temperaturein refluxing 2-propanol

Sources & evidence

ORD record
ord-84acf50d819245aea9c75dc2e171b720
Source dataset
uspto-grants-2008_09
Patent number
US07423061B2

Reaction notes

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