5-Chloro-2-picolinic acid → HCID 78035252, compound

HRID 1422594Notes

Reaction equation

HRID 1422594 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([C:8]23[CH2:15][CH: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:24][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:33])[C:29]2[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][N:30]=2)=[CH:7][C:6]=1[C:8]12[CH2:15][CH:14]1[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]2

Participants

3

Reactant 2

HCID 27628725-Chloro-2-picolinic acidHCID 86675580HCID 86675580, compound

Product 1

HCID 78035252HCID 78035252, compoundYield 54.4%

Procedure

Prepared in an analogous manner as described for intermediate rac-A9a from tert-butyl (1SR,7SR)-1-(5-amino-2-chlorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (intermediate rac-A8b) (56 mg, 152 μmol) and 5-chloro-2-pyridinecarboxylic acid to give the tert-butyl (1SR,7SR)-1-(2-chloro-5-(5-chloropicolinamido)phenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (42 mg, 82.8 μmol, 54.4% yield) as a light brown oil. MS (ISP): m/z=407.2 [(M-Boc+H)+], 409.2 [(M-Boc+2+H)+] and 411.0 [(M-Boc+4+H)+].

Workup

  1. customPrepared in an analogous manner

Sources & evidence

ORD record
ord-31f7db2ab07449529b93a394c118ef79
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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