tert-Butyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate → HCID 178484228, compound

HRID 1917192Notes

Reaction equation

HRID 1917192 reaction equation
Br.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](SCC1C=CC=CC=1)=[NH:8].[NH2:17][C:18]1[CH:19]=[CH:20][C:21]2[N:26]([CH2:27][CH2:28][N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25][CH2:24][S:23][C:22]=2[CH:38]=1>CCO>[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[NH:8])[NH:17][C:18]1[CH:19]=[CH:20][C:21]2[N:26]([CH2:27][CH2:28][N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:25][CH2:24][S:23][C:22]=2[CH:38]=1

Participants

4

Reactant 2

HCID 59144160tert-Butyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamateHCID 66704617Benzyl furan-2-carbimidothioate hydrobromide

Product 1

HCID 178484228HCID 178484228, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl furan-2-carbimidothioate hydrobromide (1.199 g, 4.02 mmol) was added to a mixture of tert-butyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate (0.763 g, 2.361 mmol) in EtOH (20 mL). The mixture was stirred under room temperature overnight. The mixture was quenched with saturated sodium bicarbonate solution (50 mL), diluted with water (50 mL), and extracted with CH2Cl2 (2×50 mL). The organic phase was washed with brine (50 mL) and dried (Na2SO4). The crude material was subject to flash chromatography on silica gel (2.5-5% (2M NH3 in MeOH):CH2Cl2). The collected fractions were concentrated to give a white foam (0.88 g, 90%). 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.44 (s, 1H), 6.74-6.69 (m, 1H), 6.62 (d, J=7.5 Hz, 1H), 4.72 (brs, 2H), 3.64-3.60 (m, 2H), 3.41 (s, 4H), 3.04-3.01 (m, 2H), 2.92 (s, 3H), 1.45 (s, 9H); ESI-MS (m/z, %): 419, 417 (MH+, 100).

Workup

  1. customThe mixture was quenched with saturated sodium bicarbonate solution (50 mL)
  2. additiondiluted with water (50 mL)
  3. extractionextracted with CH2Cl2 (2×50 mL)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationThe collected fractions were concentrated

Sources & evidence

ORD record
ord-a7826d44e8c74690969370a11f350dae
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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