tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate → Hydrochloric Acid

HRID 1962461Notes

Reaction equation

HRID 1962461 reaction equation
C(OC([N:8]([C@@H:10]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[C:19]3[C:20]([F:29])=[CH:21][N:22]=[C:23]([Cl:28])[C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:17])=[O:16])[CH2:11]1)[CH3:9])=O)(C)(C)C.ClC1C2C=CC=C(S(Cl)(=O)=[O:42])C=2C(F)=CN=1.C(OC(N([C@@H]1CCNC1)C)=O)(C)(C)C.ClC1C2C=CC=C(S(Cl)(=O)=O)C=2C(Br)=CN=1.C(OC(N([C@H]1CCNC1)C)=O)(C)(C)C>>[OH:42][C:23]1[C:24]2[CH:25]=[CH:26][CH:27]=[C:18]([S:15]([N:12]3[CH2:13][CH2:14][C@@H:10]([NH:8][CH3:9])[CH2:11]3)(=[O:17])=[O:16])[C:19]=2[C:20]([F:29])=[CH:21][N:22]=1.[ClH:28]

Participants

7

Reactant 5

HCID 7019173tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamateHCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterHCID 768514905-Isoquinolinesulfonyl chloride,4-bromo-1-chloro-HCID 86613860(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(1-chloro-4-fluoro-5-isoquinolinesulfonyl)pyrrolidine2×HCID 866138611-Chloro-4-fluoro-5-isoquinolinesulfonyl chloride

Product 2

HCID 313Hydrochloric AcidHCID 178484870HCID 178484870, compound

Procedure

(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(1-chloro-4-fluoro-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 27b) can be prepared by using 1-chloro-4-fluoro-5-isoquinolinesulfonyl chloride and (R)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine in the method of Example 35-1, Step A instead of 1-chloro-4-bromo-5-isoquinolinesulfonyl chloride and (S)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine, respectively, and then used in the method of Example 35-1, Step B in a similar manner to obtain the title compound as hydrochloride.

Sources & evidence

ORD record
ord-7004280368e64773a32ce6cc214ab6bb
Source dataset
uspto-grants-2013_04
Patent number
US08415372B2

Reaction notes

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