Tetrahydrofuran → HCID 90014762, compound

HRID 930964Notes

Reaction equation

HRID 930964 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[C:9]3[C:14]([NH:15][C:16]4[CH:25]=[CH:24][C:19]5[NH:20][C:21](=[O:23])[S:22][C:18]=5[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[S:26][C:5]=2[CH2:4]1.O1CCCC1.P([N:48]=[N+:49]=[N-:50])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.N1CCCN2CCCCCC=12>O>[N:48]([CH2:2][CH:3]1[CH2:8][CH2:7][C:6]2[C:9]3[C:14]([NH:15][C:16]4[CH:25]=[CH:24][C:19]5[NH:20][C:21](=[O:23])[S:22][C:18]=5[CH:17]=4)=[N:13][CH:12]=[N:11][C:10]=3[S:26][C:5]=2[CH2:4]1)=[N+:49]=[N-:50]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 90014767HCID 90014767, compound

Product 1

HCID 90014762HCID 90014762, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 3.05 g (7.93 mmol) (RS)-6-{[7-(hydroxymethyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl]amino}-1,3-benzothiazol-2(3H)-one (prepared according to example 18), 140 mL tetrahydrofuran, 2.91 mL diphenyl phosphorazidate and 1.66 mL 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine was heated in a pressure tube at 100° C. overnight. Water was added, the mixture extracted with ethylacetate, the combined organic layers were washed with brine and dried over sodium sulphate. After filtration and removal of the solvents, the residue was purified by crystallization from ethanol to give 2.01 g (62%) of the title compound.

Workup

  1. extractionthe mixture extracted with ethylacetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationAfter filtration and removal of the solvents
  5. customthe residue was purified by crystallization from ethanol

Sources & evidence

ORD record
ord-a50183e3baec4821a6be96fd58abebdf
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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