6-Aminobenzothiazole → HCID 66921510, compound

HRID 1364308Notes

Reaction equation

HRID 1364308 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C.CCCP(=O)=O>CN(C=O)C.O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:25])[NH:10][C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 682886-AminobenzothiazoleHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 16167369Propylphosphoric anhydride

Product 1

HCID 66921510HCID 66921510, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of benzothiazol-6-ylamine (0.15 g, 1 mmol) and piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (0.23 g, 1 mmol) in DMF (3 ml) was treated with DIPEA (5 eq.) and propylphosphonic anhydride (1 eq, 50% solution in EA). The mixture was stirred at rt for 72 h, diluted with water and extracted with EA. The org. layers were washed with water and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (hex/EA 1:1, EA) to give the coupling product as a colourless oil (0.22 g, 61% yield).

Workup

  1. extractionextracted with EA
  2. washlayers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on SiO2 (hex/EA 1:1, EA)

Sources & evidence

ORD record
ord-b4de2e7a09e94650bfa65e3080edaab5
Source dataset
uspto-grants-2011_02
Patent number
US07888359B2

Reaction notes

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