Methyl 6,6-difluoro-8-azabicyclo[3.2.1]octane-3-carboxylate → HCID 117697779, compound

HRID 1778556Notes

Reaction equation

HRID 1778556 reaction equation
[F:1][C:2]1([F:14])[CH2:8][CH:7]2[NH:9][CH:3]1[CH2:4][CH:5]([C:10]([O:12]C)=[O:11])[CH2:6]2.Br[CH2:16][C:17]1[NH:22][C:21]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[N:20][C@@H:19]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=2[Cl:35])[C:18]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]>>[Cl:35][C:29]1[C:30]([F:34])=[CH:31][CH:32]=[CH:33][C:28]=1[C@H:19]1[C:18]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:17]([CH2:16][N:9]2[CH:3]3[C:2]([F:14])([F:1])[CH2:8][CH:7]2[CH2:6][CH:5]([C:10]([OH:12])=[O:11])[CH2:4]3)[NH:22][C:21]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[N:20]1

Participants

3

Reactant 2

HCID 117706760Methyl 6,6-difluoro-8-azabicyclo[3.2.1]octane-3-carboxylateHCID 118358749Ethyl (R)-6-(bromomethyl)-4-(2-chloro-3-fluorophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 117697779HCID 117697779, compoundYield 6%

Procedure

The title compound was prepared in analogy to Example 1, by using methyl 6,6-difluoro-8-azabicyclo[3.2.1]octane-3-carboxylate 150a (200 mg) and ethyl (4R)-6-(bromomethyl)-4-(2-chloro-3-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate 98a (400 mg). 30 mg of the title compound was isolated finally after preparative HPLC purification. Preparation of methyl 6,6-difluoro-8-azabicyclo[3.2.1]octane-3-carboxylate 150a:

Workup

  1. customThe title compound was prepared in analogy to Example 1

Sources & evidence

ORD record
ord-cecd450ee3424ffa8703e8dfb506d8d2
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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