tert-Butyl 3-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)pyrrolidine-1-carboxylate → HCID 178452061, compound

HRID 424590Notes

Reaction equation

HRID 424590 reaction equation
I.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](SC)=[NH:8].[NH2:11][C:12]1[CH:13]=[CH:14][C:15]2[N:20]([CH:21]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]3)[CH2:19][CH2:18][S:17][C:16]=2[CH:33]=1>CCO>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[NH:8])[NH:11][C:12]1[CH:13]=[CH:14][C:15]2[N:20]([CH:21]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:22]3)[CH2:19][CH2:18][S:17][C:16]=2[CH:33]=1

Participants

4

Reactant 2

HCID 59144157tert-Butyl 3-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)pyrrolidine-1-carboxylateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178452061HCID 178452061, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl thiophene-2-carbimidothioate hydroiodide (0.53 g, 1.874 mmol) was added to a mixture of tert-butyl 3-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)pyrrolidine-1-carboxylate (0.31 g, 0.937 mmol) in EtOH (20 mL). The mixture was stirred under room temperature overnight. The mixture was quenched with saturated sodium bicarbonate solution (50 mL). The solution was then transferred to a separatory funnel, diluted with water (50 mL), and extracted with CH2Cl2 (2×50 mL). The crude material was subjected to flash chromatography on silica gel (50-90% EtOAc/hexanes). The concentrated fractions afforded a yellow oil (0.29 g, 69%). 1H NMR (CDCl3) δ 7.41 (dd, J=0.9, 5.1 Hz, 1H), 7.38 (d, J=3.6 Hz, 1H), 7.06 (dd, J=3.9, 4.9 Hz, 1H), 6.79-6.76 (m, 2H), 6.68-6.66 (m, 1H), 4.84 (brs, 2H), 4.35-4.23 (m, 1H), 3.74-3.22 (m, 6H), 3.12-3.07 (m, 2H), 2.19-1.99 (m, 2H), 1.47 (s, 9H); ESI-MS (m/z, %): 447, 445 (MH+, 100).

Workup

  1. customThe mixture was quenched with saturated sodium bicarbonate solution (50 mL)
  2. customThe solution was then transferred to a separatory funnel
  3. additiondiluted with water (50 mL)
  4. extractionextracted with CH2Cl2 (2×50 mL)

Sources & evidence

ORD record
ord-207f8126bd2b4cdbafb5e19809f2ef9b
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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