Methanesulfonic Acid → (S)-3-amino-2-(4-chlorophenyl)-N-(isoquinolin-6-yl)propanamide dimesylate salt

HRID 1482738Notes

Reaction equation

HRID 1482738 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:18]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)=[O:19])[CH2:9][NH:10]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.[S:31]([OH:35])([CH3:34])(=[O:33])=[O:32]>C(Cl)Cl>[S:31]([OH:35])(=[O:33])(=[O:32])[CH3:34].[S:31]([OH:35])(=[O:33])(=[O:32])[CH3:34].[NH2:10][CH2:9][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[N:26][CH:25]=[CH:24]2)=[O:19]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 90412140(S)-tert-butyl 2-(4-chlorophenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate

Product 1

HCID 90411822(S)-3-amino-2-(4-chlorophenyl)-N-(isoquinolin-6-yl)propanamide dimesylate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-tert-butyl 2-(4-chlorophenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (29, 7.8 g) was added CH2Cl2 and MsOH and the solution was stirred overnight at room temperature. The solvents were evaporated and the crude 30 was dried on the high vacuum. Recrystallization (isopropanol) and drying on the high vacuum gave pure (S)-3-amino-2-(4-chlorophenyl)-N-(isoquinolin-6-yl)propanamide dimesylate salt (30, 7.2 g, 77%, >99% S-enantiomer).

Workup

  1. customThe solvents were evaporated
  2. customthe crude 30 was dried on the high vacuum
  3. customRecrystallization (isopropanol)
  4. customdrying on the high vacuum

Sources & evidence

ORD record
ord-d7a55536375844dcacfe60fed9f1938d
Source dataset
uspto-grants-2016_08
Patent number
US09415043B2

Reaction notes

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