Hydrochloric Acid → HCID 178465185, compound

HRID 1420315Notes

Reaction equation

HRID 1420315 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])=[C:4]([NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1.[NH2:38][CH2:39][CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=1.Cl>CS(C)=O.C(OCC)(=O)C.CO>[ClH:1].[C:26]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][NH:23][C:4]2[N:3]=[C:2]([NH:38][CH2:39][CH2:40][C:41]3[N:45]=[CH:44][NH:43][CH:42]=3)[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[C@@H:11]2[O:17][C@H:16]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 86647542HCID 86647542, compoundHCID 178419017HCID 178419017, compound

Product 1

HCID 178465185HCID 178465185, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-β-D-ribofuranuronamide (0.155 g, 0.296 mmol) and histamine (0.22 g) in dimethylsulphoxide (1.5 ml) was heated at 120° C. for 16 h. The mixture was cooled and diluted with ethyl acetate (50 ml) then washed with water (50 ml). The aqueous phase was extracted with ethyl acetate (50 ml) and the combined organic phase was washed with water (50 ml), dried (MgSO4) and evaporated to leave a solid which was treated with 2N hydrochloric acid (2 ml) in methanol (30 ml) and the solution was evaporated to leave the title compound (0.15 g, 80%) as a solid. MH+ =598, nmr(δ,DMSO-d6) includes 1.02(t,3H), 3.0(m,2H), 3.13(m,2H), 3.7(m,2H), 4.2(m,2H), 4.85(s,1H), 4.55(m,3H), 5.9(d,1H), 7.1-7.6(m,12H), 8.45(s,1H), 9.05(s,1H), 14.3(m,1H).

Workup

  1. temperatureThe mixture was cooled
  2. washthen washed with water (50 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
  4. washthe combined organic phase was washed with water (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto leave a solid which
  8. customthe solution was evaporated

Sources & evidence

ORD record
ord-7805c65124884acbbd98ab0c26cd120a
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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