1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-Butyl 6-[[[6-(8-methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]carbonyl]amino]hexylcarbamate

HRID 499503Notes

Reaction equation

HRID 499503 reaction equation
[CH3:1][C:2]1[C:11]2[S:10][C:9]([C:12]3[N:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][CH:13]=3)=[N:8][C:7](=[O:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:28])([CH3:25])([CH3:24])[CH3:23].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(OCC)(=O)C>[CH3:1][C:2]1[C:11]2[S:10][C:9]([C:12]3[N:17]=[C:16]([C:18]([NH:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][NH:29][C:27](=[O:28])[O:26][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH:15]=[CH:14][CH:13]=3)=[N:8][C:7](=[O:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2733170N-BOC-1,6-diaminohexaneHCID 229393756-(8-Methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylic acid

Product 1

HCID 22939618tert-Butyl 6-[[[6-(8-methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]carbonyl]amino]hexylcarbamateYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

6-(8-Methyl-4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylic acid (1.5 g, 5.0 mmol) was dissolved in DMF (15 ml), and N-(tert-butoxycarbonyl)-1,6-diaminohexane (2.1 g, 10.0 mmol), WSC (3.0 g, 15.5 mmol) and HOBt (2.0 g, 14.9 mmol) were added thereto. The reaction mixture was stirred at 80° C. for 10 hrs and combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-hexane (4:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (1.1 g, 45%) as white crystals.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with ethyl acetate-hexane (4:1
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-21c75d0babff4817822e09d885825ea7
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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