Hydrochloric Acid → (5R,7R)-4-(3-(2-amino-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol trihydrochloride

HRID 521396Notes

Reaction equation

HRID 521396 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[C:22]3[CH:23]=[CH:24][C:25]([C:27]4[C:28]5[C@H:35]([CH3:36])[CH2:34][C@@H:33]([OH:37])[C:29]=5[N:30]=[CH:31][N:32]=4)=[CH:26][C:21]=3[S:20][N:19]=2)[CH2:9][NH:10]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.[ClH:38]>C(Cl)Cl.O1CCOCC1>[ClH:1].[ClH:38].[ClH:1].[NH2:10][CH2:9][CH:8]([C:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]3[C:28]4[C@H:35]([CH3:36])[CH2:34][C@@H:33]([OH:37])[C:29]=4[N:30]=[CH:31][N:32]=3)=[CH:26][C:21]=2[S:20][N:19]=1)[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67438914tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate

Product 1

HCID 67436726(5R,7R)-4-(3-(2-amino-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol trihydrochlorideYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 2-(4-chlorophenyl)-2-(6-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)benzo[d]isothiazol-3-yl)ethylcarbamate (41 mg, 0.076 mmol) in DCM was treated with 4N HCl in dioxane (0.5 mL). The reaction was stirred at room temperature overnight. The reaction was concentrated and triturated with ether (twice) to yield (5R,7R)-4-(3-(2-amino-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol trihydrochloride (32 mg, 77%). LCMS (APCI+) m/z 437, 439 [M+H]+; Rt=2.48 min.

Workup

  1. concentrationThe reaction was concentrated
  2. customtriturated with ether (twice)

Sources & evidence

ORD record
ord-d1f88d0a6f244bcd9e3fd5de324f5f40
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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