Hydrochloric Acid → HCID 86686873, compound

HRID 2406279Notes

Reaction equation

HRID 2406279 reaction equation
[N+]12([S:9]([N-:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(=[O:11])=[O:10])CCN(CC1)CC2.N12CCN(CC1)CC2.Cl.[Cl:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[C@@H:35]([NH:39][C:40]1[N:45]=[CH:44][N:43]=[C:42]([O:46][C@H:47]3[CH2:51][C@H:50]([OH:52])[C@H:49]([CH2:53][OH:54])[CH2:48]3)[CH:41]=1)[C@@H:34]([O:55][CH3:56])[CH2:33]2.O>C(#N)C.CN1CCCC1=O.C(OCC)(=O)C>[Cl:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[C@@H:35]([NH:39][C:40]1[N:45]=[CH:44][N:43]=[C:42]([O:46][C@@H:47]3[CH2:48][C@@H:49]([CH2:53][O:54][S:9]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])(=[O:10])=[O:11])[C@@H:50]([OH:52])[CH2:51]3)[CH:41]=1)[C@@H:34]([O:55][CH3:56])[CH2:33]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 71270619HCID 71270619, compoundHCID 178420725HCID 178420725, compound

Product 1

HCID 86686873HCID 86686873, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (4-aza-1-azoniabicyclo[2.2.2]oct-1-ylsulfonyl)(tert-butoxycarbonyl)azanide-1,4-diazabicyclo[2.2.2]octane (1:1) hydrochloride (43.4 g, 98.6 mmol) in acetonitrile (30 mL), in a 500 mL reactor, was added (1S,2S,4R)-4-(6-((1R,2S)-5-chloro-2-methoxy-2,3-dihydro-1H-inden-1-ylamino)pyrimidin-4-yloxy)-2-(hydroxymethyl)cyclopentanol (27) (10 g, 24.6 mmol) in N-methylpyrrolidinone (60 mL). The resultant thick slurry was stirred at ambient temperature for 3 hours. Upon reaction completion, water (66.6 mL) was added slowly at ambient temperature. To the resulting mixture, ethyl acetate (66.7 mL) was added. The aqueous layer was extract three times with ethyl acetate (3×66.6 mL). The combined organic layers were washed once with water (66.7 mL) and once with saturated sodium chloride in water (66.7 mL). The combined organic layers were dried over magnesium sulfate (3 g), filtered and concentrated. This product was taken on to the next step without further purification.

Workup

  1. additionwas added slowly at ambient temperature
  2. extractionThe aqueous layer was extract three times with ethyl acetate (3×66.6 mL)
  3. washThe combined organic layers were washed once with water (66.7 mL) and once with saturated sodium chloride in water (66.7 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate (3 g)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis product was taken on to the next step without further purification

Sources & evidence

ORD record
ord-390633093b1843ad8b7052e172654804
Source dataset
uspto-grants-2014_08
Patent number
US08809356B2

Reaction notes

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