Hydrochloric Acid → HCID 72547965, compound

HRID 879170Notes

Reaction equation

HRID 879170 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 86705217HCID 86705217, compound

Product 1

HCID 72547965HCID 72547965, compoundYield 94%

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,2S,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,4S,5S)-3-amino-5-methyl-4-(methylthio)cyclohexyl)pyridin-3-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide in 94% yield. LC/MS (m/z)=487.2 (MH+), Rt=0.65 min. 1H NMR (400 MHz, <dmso>) δ ppm 10.44 (s, 1H), 8.58 (d, J=4.0, 1H), 8.47 (d, J=4.0, 1H), 8.34 (dd, J=8.0, 4.0, 1H), 8.20 (dd, J=8.0, 8.0, 1H), 8.20 (dd, J=16.0, 4.0, 1H), 7.67-7.74 (m, 1H), 7.36 (dd, J=8.0, 8.0, 2H), 7.26 (d, J=4.0, 1H), 2.85-2.95 (m, 2H), 2.18 (s, 3H), 1.88-1.98 (m, 1H), 1.74-1.84 (m, 1H), 1.48-1.56 (m, 1H), 1.38-1.48 (m, 1H), 1.18-1.28 (m, 1H), 1.02 (d, J=8.0, 3H).

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-b42226b059c24014b2b4ce02b90b3c20
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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