5-Chloro-2-picolinic acid → HCID 71202301, compound

HRID 1422592Notes

Reaction equation

HRID 1422592 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C@:8]23[CH2:15][C@H:14]2[CH2:13][CH2:12][S:11][C:10]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:9]3)[CH:7]=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32](O)=[O:33])=[N:30][CH:31]=1>>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C@:8]34[CH2:15][C@H:14]3[CH2:13][CH2:12][S:11][C:10]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[N:9]4)[CH:7]=2)=[O:33])=[N:30][CH:31]=1

Participants

3

Reactant 2

HCID 27628725-Chloro-2-picolinic acidHCID 86675579HCID 86675579, compound

Product 1

HCID 71202301HCID 71202301, compoundYield 50%

Procedure

Prepared in an analogous manner as described for intermediate rac-A9a from tert-butyl (1S,7S)-1-(5-amino-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (intermediate (−)-A8a) (85 mg, 0.24 mmol) and 5-chloro-2-pyridinecarboxylic acid to give the tert-butyl (1S,7S)-1-(5-(5-chloropicolinamido)-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (70 mg, 50% yield) as a light yellow oil. MS (ISP): m/z=391.0 [(M-Boc+H)+] and 393.1 [(M-Boc+2+H)+].

Workup

  1. customPrepared in an analogous manner

Sources & evidence

ORD record
ord-4fceff475c014ad18305bfe0114fbee2
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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