Hydrochloric Acid → HCID 16058696, compound

HRID 733687Notes

Reaction equation

HRID 733687 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[ClH:7].[CH3:8][N:9]([CH3:18])[CH2:10][CH2:11][CH2:12][N:13]=[C:14]=[N:15][CH2:16][CH3:17].O.ON1C2C=[CH:27][CH:28]=[CH:29][C:24]=2N=N1.C(N([CH2:37][CH3:38])C(C)C)(C)C.[C:39](=[O:42])(O)[O-].[Na+].Cl>CN(C)C=O.C(Cl)Cl.C(OCC)(=O)C>[ClH:7].[Cl:7][C:27]1[CH:17]=[C:16]([NH:15][C:14]2[C:37]3[CH:38]=[CH:18][N:9]([CH3:8])[C:10]=3[C:11]([C:39]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:42])=[CH:12][N:13]=2)[CH:24]=[CH:29][CH:28]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 16058696HCID 16058696, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-chloro-phenylamino)-1H-methyl-1H-pyrrolo[3,2-c]pyridin-7-carboxylic acid (29 mg), morpholine (36 ul), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (76 mg), 1-hydroxybenzotriazole hydrate (54 mg) and N,N-diisopropylethylamine (140 ul) in dimethylformamide (2 ml) was stirred overnight then added to a mixture of ethyl acetate (20 ml) water (20 ml) and saturated sodium bicarbonate (10 ml). The layers were separated and the organic layer washed with water 3 times, brine, dried (MgSO4) and evaporated to give a gum. Purified on MDAP and the product split into two fractions. The first fraction was evaporated, dissolved in ethyl acetate and washed as above, dried and evaporate to give a solid. This was triturated with ether and purified by MDAP and chromatography on silica gel, eluting with dichloromethane/methanol, 20:1, to give the free base which was taken up in DCM treated with ethereal HCl, evaporated and triturated with ether to give the title compound as a solid (11 mg)

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with water 3 times, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a gum
  6. customPurified on MDAP
  7. customthe product split into two fractions
  8. customThe first fraction was evaporated
  9. dissolutiondissolved in ethyl acetate
  10. washwashed as above,
  11. customdried
  12. customevaporate
  13. customto give a solid
  14. customThis was triturated with ether
  15. custompurified by MDAP and chromatography on silica gel
  16. washeluting with dichloromethane/methanol, 20:1
  17. customto give the free base which
  18. customevaporated
  19. customtriturated with ether

Sources & evidence

ORD record
ord-757ddea0f33d4866ba1fbbf2c7156c96
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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