Pyridine → HCID 57663157, compound

HRID 548749Notes

Reaction equation

HRID 548749 reaction equation
ClC(N(C)C)=C(C)C.[O:9]=[S:10]1(=[O:37])[C:16]2[CH:17]=[CH:18][C:19]([O:21][C:22]3[CH:23]=[C:24]([CH:28]=[C:29]([O:31][C@@H:32]([CH3:36])[CH2:33][O:34][CH3:35])[CH:30]=3)[C:25](O)=[O:26])=[CH:20][C:15]=2[O:14][CH2:13][CH2:12][NH:11]1.[NH2:38][C:39]1[CH:43]=[CH:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[N:40]=1.N1C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C.O>[O:37]=[S:10]1(=[O:9])[C:16]2[CH:17]=[CH:18][C:19]([O:21][C:22]3[CH:23]=[C:24]([C:25]([NH:38][C:39]4[CH:43]=[CH:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[N:40]=4)=[O:26])[CH:28]=[C:29]([O:31][C@@H:32]([CH3:36])[CH2:33][O:34][CH3:35])[CH:30]=3)=[CH:20][C:15]=2[O:14][CH2:13][CH2:12][NH:11]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 51358380tert-Butyl 3-amino-1H-pyrazole-1-carboxylateHCID 576632223-[(1,1-dioxido-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl)oxy]-5-{[(S)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid

Product 1

HCID 57663157HCID 57663157, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1-Chloro-N,N,2-trimethyl-1-propenylamine (0.1 mL, 0.74 mmol) was added to a solution of 3-[(1,1-dioxido-3,4-dihydro-2H-5,1,2-benzoxathiazepin-7-yl)oxy]-5-{[(S)-1-methyl-2-(methyloxy)ethyl]oxy}benzoic acid (0.21 g, 0.50 mmol) in DCM (5 mL) and stirred for 1 hour. 1,1-Dimethylethyl 3-amino-1H-pyrazole-1-carboxylate (137 mg, 0.74 mmol) then pyridine (0.08 mL, 0.99 mmol) were added and the reaction stirred for a further 45 minutes. The mixture was reduced in vacuo and ethyl acetate (50 mL) and water (50 mL) added. The aqueous layer was re-extracted into ethyl acetate (50 mL) and the combined organics washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and reduced in vacuo to give a golden oil which was chromatographed on silica, eluting with 30-60% ethyl acetate in isohexane, to give a colourless oil. The oil was dissolved in ethyl acetate (30 mL) and washed with 1M hydrochloric acid, dried (MgSO4), filtered and reduced in vacuo to give the desired compound as a colourless oil (47 mg).

Workup

  1. stirringthe reaction stirred for a further 45 minutes
  2. additionadded
  3. extractionThe aqueous layer was re-extracted into ethyl acetate (50 mL)
  4. washthe combined organics washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customto give a golden oil which
  8. customwas chromatographed on silica
  9. washeluting with 30-60% ethyl acetate in isohexane
  10. customto give a colourless oil
  11. washwashed with 1M hydrochloric acid
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered

Sources & evidence

ORD record
ord-c7bae9d0be03412ca40e2291f6a90484
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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