Hydrochloric Acid → HCID 72547733, compound

HRID 879176Notes

Reaction equation

HRID 879176 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:4]=1[C:10]1[N:15]=[C:14]([C:16]([NH:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][C:24]=2[C@H:25]2[CH2:30][C@@H:29]([NH:31]C(=O)OC(C)(C)C)[C@H:28]([S:39][CH3:40])[C@@H:27]([CH3:41])[CH2:26]2)=[O:17])[CH:13]=[CH:12][C:11]=1[F:42]>O1CCOCC1>[NH2:31][C@H:29]1[C@H:28]([S:39][CH3:40])[C@@H:27]([CH3:41])[CH2:26][C@@H:25]([C:24]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[NH:18][C:16](=[O:17])[C:14]2[CH:13]=[CH:12][C:11]([F:42])=[C:10]([C:4]3[C:3]([F:2])=[CH:8][CH:7]=[CH:6][C:5]=3[F:9])[N:15]=2)[CH2:30]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86705221HCID 86705221, compound

Product 1

HCID 72547733HCID 72547733, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of HCl (30.0 equiv.) in dioxane was added to tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-3-methyl-2-(methylthio)cyclohexylcarbamate (1.0 equiv.). The solution was capped and left standing at rt for 1 hr. The volatiles were removed in vacuo, dissolved in DMSO and purified by reverse phase HPLC to yield N-(4-((1R,3R,4R,5S)-3-amino-5-methyl-4-(methylthio)cyclohexyl)pyridin-3-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide in 43% yield. LC/MS (m/z)=487.2 (MH+), Rt=0.65 min.

Workup

  1. customThe solution was capped
  2. waitleft
  3. customThe volatiles were removed in vacuo
  4. dissolutiondissolved in DMSO
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-0c47a363e8e94dcfa1da73c026ddad7e
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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