3-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine → Hydrochloric Acid

HRID 1436043Notes

Reaction equation

HRID 1436043 reaction equation
[F:1][C:2]1[C:11]2[C:10]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[N:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]([C@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1)[CH3:24])=[O:22])([CH3:19])([CH3:18])[CH3:17].BrC1C2C(S(Cl)(=O)=O)=CC=CC=2C=NC=1.C(OC(N(C1CCNC1)C)=O)(C)(C)C>>[C:16]([O:20][C:21]([N:23]([C@H:25]1[CH2:29][CH2:28][N:27]([S:12]([C:10]2[C:11]3[C:2]([F:1])=[CH:3][N:4]=[CH:5][C:6]=3[CH:7]=[CH:8][CH:9]=2)(=[O:14])=[O:13])[CH2:26]1)[CH3:24])=[O:22])([CH3:19])([CH3:17])[CH3:18].[ClH:15]

Participants

6

Reactant 4

HCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidineHCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterHCID 118565474-Fluoroisoquinoline-5-sulfonylchlorideHCID 145800584-Bromo-5-isoquinolinesulfonyl chloride

Product 2

HCID 313Hydrochloric AcidHCID 67242681(S)-3-[N-(tert-butoxycarbonyl)-N-methylamino]-1-(4-fluoro-5-isoquinolinesulfonyl)pyrrolidine

Procedure

That is, (S)-3-[N-(tert-butoxycarbonyl)-N-methylamino]-1-(4-fluoro-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 22a) was prepared by using 4-fluoro-5-isoquinolinesulfonyl chloride and (S)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine in the method of Example 31, Step A instead of 4-bromo-5-isoquinolinesulfonyl chloride and 3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine, respectively, and then used in the method of Example 31, Step B in a similar manner to obtain the compound of Example 18-3 as hydrochloride.

Sources & evidence

ORD record
ord-00042accdd0842d3bf0b2a64cef55b4a
Source dataset
uspto-grants-2009_11
Patent number
US07618984B2

Reaction notes

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