6-Bromo-5-fluoropicolinic Acid → (1R,2R,4R,6S)-4-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate

HRID 1523527Notes

Reaction equation

HRID 1523527 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([CH3:11])[CH2:9][C@@H:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH2:18])[CH2:7][C@H:6]1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])(=[O:3])[CH3:2].[Br:27][C:28]1[N:33]=[C:32]([C:34](O)=[O:35])[CH:31]=[CH:30][C:29]=1[F:37]>CCOC(C)=O>[C:1]([O:4][C@@H:5]1[C@@H:10]([CH3:11])[CH2:9][C@@H:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[NH:18][C:34](=[O:35])[C:32]2[CH:31]=[CH:30][C:29]([F:37])=[C:28]([Br:27])[N:33]=2)[CH2:7][C@H:6]1[NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 534011946-Bromo-5-fluoropicolinic AcidHCID 68555677(1R,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl acetate

Product 1

HCID 86639736(1R,2R,4R,6S)-4-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following Method 9, (1R,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate and 6-bromo-5-fluoropicolinic acid were coupled and following addition of EtOAc and washing with H2O, NaCl(sat.) and drying over MgSO4, (1R,2R,4R,6S)-4-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)-2-(tert-butoxycarbonylamino)-6-methylcyclohexyl acetate was obtained. LCMS (m/z): 567.2 (MH+), Rt=0.82 min.

Workup

  1. washwashing with H2O, NaCl(sat.)
  2. dry with materialdrying over MgSO4

Sources & evidence

ORD record
ord-432823c7688a4a09958421c1c70f5802
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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