Hydrochloric Acid → (3R)-3-(3-Tetrahydrofuranyl)amino-1-(4-chloro-5-isoquinolinesulfonyl)pyrrolidine

HRID 2425439Notes

Reaction equation

[ClH:1].[O:2]1[CH2:6][CH2:5][C:4](=O)[CH2:3]1.[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1.C(=O)C1OC=CC=1>>[O:2]1[CH2:6][CH2:5][CH:4]([NH:8][C@@H:9]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[C:18]4[C:19]([Cl:1])=[CH:20][N:21]=[CH:22][C:23]=4[CH:24]=[CH:25][CH:26]=3)(=[O:16])=[O:15])[CH2:10]2)[CH2:3]1

Participants

Reactant 4

HCID 313Hydrochloric Acid2×

HCID 7362Furfural

HCID 5293923-Oxotetrahydrofuran

HCID 16223985(S)-3-Amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

Product 1

HCID 67245551(3R)-3-(3-Tetrahydrofuranyl)amino-1-(4-chloro-5-isoquinolinesulfonyl)pyrrolidine

Procedure

Hydrochloride of the compound obtained in Example 19-2 and tetrahydrofuran-3-one can be used in the method of Example 4-1 instead of hydrochloride of (S)-3-amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine and furfural, respectively, to obtain the title compound.

Sources & evidence

ORD record: ord-7e55eb1be6634e2fb4e1a00ca552df92
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964613B2

Reaction notes

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