(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester → (5)-Tert-butyl (1-(3-bromo-5-((4-(trifluoromethoxy)phenyl)carbamoyl)pyridin-2-yl)pyrrolidin-3-yl)(methyl)carbamate

HRID 923927Notes

Reaction equation

HRID 923927 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:23][N:24]([C@H:32]1[CH2:36][CH2:35][NH:34][CH2:33]1)[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>>[Br:1][C:2]1[C:3]([N:34]2[CH2:35][CH2:36][C@H:32]([N:24]([CH3:23])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:33]2)=[N:4][CH:5]=[C:6]([C:7](=[O:8])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118198937(5)-Tert-butyl (1-(3-bromo-5-((4-(trifluoromethoxy)phenyl)carbamoyl)pyridin-2-yl)pyrrolidin-3-yl)(methyl)carbamate

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 93.1 using 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2) and (S)-tert-butyl methyl(pyrrolidin-3-yl)carbamate. LC-MS (Condition 6) tR=1.59 min, m/z=558.8/560.8 [M+H]+, m/z=502.9/504.9 [M+H—H2C═C(CH3)2].

Sources & evidence

ORD record
ord-857ce244e49f496da5cce3d623758c3a
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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