3-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine → Hydrochloric Acid
Reaction equation
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[C:5]([F:16])=[CH:4][N:3]=1.[C:17]([O:21][C:22]([N:24]([C@@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)[CH3:25])=[O:23])([CH3:20])([CH3:19])[CH3:18].[Cl:31]C1C2C=CC=C(S(Cl)(=O)=[O:43])C=2C(Br)=CN=1.C(O[C:52]([N:54]([CH:56]1[CH2:60][CH2:59][NH:58][CH2:57]1)C)=O)(C)(C)C>>[C:17]([O:21][C:22]([N:24]([C@@H:26]1[CH2:30][CH2:29][N:28]([S:12]([C:7]2[C:6]3[C:5]([F:16])=[CH:4][N:3]=[C:2]([Cl:1])[C:11]=3[CH:10]=[CH:9][CH:8]=2)(=[O:14])=[O:13])[CH2:27]1)[CH3:25])=[O:23])([CH3:20])([CH3:18])[CH3:19].[OH:43][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([N:58]3[CH2:59][CH2:60][C@@H:56]([NH:54][CH3:52])[CH2:57]3)(=[O:14])=[O:13])[C:6]=2[C:5]([F:16])=[CH:4][N:3]=1.[ClH:31]Participants
7
Reactant 4
Product 3
Procedure
(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(1-chloro-4-fluoro-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 27b) is prepared by using 1-chloro-4-fluoro-5-isoquinolinesulfonyl chloride and (R)-3-[N-(tert-butoxy-carbonyl)-N-methylamino]pyrrolidine in the method of Example 35, Step A instead of 1-chloro-4-bromo-5-isoquinolinesulfonyl chloride and 3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine, respectively, and then used in the method of Example 35, Step B in a similar manner to obtain the title compound as hydrochloride.
Sources & evidence
- ORD record
- ord-5898350fbe1642688eb02f66d9a5eb81
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618984B2
Reaction notes
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