Water → Ammonia

HRID 2289794Notes

Reaction equation

HRID 2289794 reaction equation
Cl.ClC1C2C(=CC(S(N3CCOC(=O)C43CCCC4)(=O)=O)=CC=2)C(N=C(N)N)=[N:5]C=1.Cl.[NH2:32][C:33]([NH2:35])=[NH:34].Cl[C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([S:47]([N:50]([CH2:61][CH2:62][O:63][CH:64]3[CH2:69][CH2:68][CH2:67][CH2:66][O:65]3)[C:51]3([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH2:55][CH2:54][CH2:53][CH2:52]3)(=[O:49])=[O:48])[CH:45]=2)[C:40]([Cl:70])=[CH:39][N:38]=1.O>CS(C)=O>[NH3:5].[Cl:70][C:40]1[C:41]2[C:46](=[CH:45][C:44]([S:47]([N:50]([CH2:61][CH2:62][O:63][CH:64]3[CH2:69][CH2:68][CH2:67][CH2:66][O:65]3)[C:51]3([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH2:52][CH2:53][CH2:54][CH2:55]3)(=[O:48])=[O:49])=[CH:43][CH:42]=2)[C:37]([NH:34][C:33]([NH2:35])=[NH:32])=[N:38][CH:39]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 18698220HCID 18698220, compoundHCID 18698234HCID 18698234, compound

Product 2

HCID 222AmmoniaHCID 178470257HCID 178470257, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

N"-{4-Chloro-7-[(10-oxo-9-oxa-6-azaspiro [4.5]dec-6-yl)sulphonyl]-1-isoquinolinyl}guanidine hydrochloride ##STR98## NaH (45 mg, 80% dispersion in mineral oil, 1.5 mmol) was added to a solution of guanidine hydrochloride (231 mg, 2.4 mmol) in DMSO (5 ml), and the solution stirred at 50° C. for 20 min. Ethyl 1-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl][2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}cyclopentanecarboxylate (330 mg, 0.6 mmol) was added and the reaction stirred at 70° C. for 21/2 h. The cooled reaction was poured into water, extracted with EtOAc, and the combined organic extracts washed with brine, dried (MgSO4) and evaporated in vacuo. The residual yellow gum was purified by column chromatography upon silica gel using CH2Cl2 -MeOH-0.880 NH3 (95:5:0.5) as eluant to give ethyl 1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl][2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino}cyclopentanecarboxylate as an orange oil.

Workup

  1. stirringthe reaction stirred at 70° C. for 21/2 h
  2. customThe cooled reaction
  3. extractionextracted with EtOAc
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residual yellow gum was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-0a4fb343cdfb438f9f00b0c84628b2fe
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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