Sodium Bicarbonate → HCID 178483720, compound

HRID 1917203Notes

Reaction equation

HRID 1917203 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][CH2:8][S:7][C:6]=2[CH:23]=1.I.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](SC)=[NH:31].C([O-])(O)=O.[Na+]>C(O)C>[CH3:22][N:14]([CH2:13][CH2:12][CH2:11][N:10]1[CH2:9][CH2:8][S:7][C:6]2[CH:23]=[C:2]([NH:1][C:30]([C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)=[NH:31])[CH:3]=[CH:4][C:5]1=2)[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 59144118HCID 59144118, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178483720HCID 178483720, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 3-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)propyl(methyl)carbamate (0.52 g, 1.541 mmol) in dry ethanol (20 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.879 g, 3.08 mmol) at room temperature and stirred over night (18 hours). The reaction was basified with saturated NaHCO3 solution (50 mL), and the product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layers were washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (2:98 (2 M NH3 in MeOH):CH2Cl2) on silica gel to obtain the title product (0.60 g, 87%) as a solid. ESI-MS (m/z, %): 447 (MH+, 100).

Workup

  1. extractionthe product was extracted into CH2Cl2 (2×25 mL)
  2. washThe combined CH2Cl2 layers were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customthe crude material was purified by column chromatography (2:98 (2 M NH3 in MeOH):CH2Cl2) on silica gel

Sources & evidence

ORD record
ord-829a1b1d990e48aabfee665fff6269d1
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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