HCID 90042588, compound → HCID 90067422, compound

HRID 929245Notes

Reaction equation

HRID 929245 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:24][C:23]([O:25][C@@H:26]3[CH2:30][O:29][C@@H:28]4[C@H:31]([OH:34])[CH2:32][O:33][C@H:27]34)=[N:22][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:15][CH2:16][S:17](=[O:21])(=[O:20])[CH2:18][CH:19]=2)=[CH:10][CH:9]=1.[H][H]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:24][C:23]([O:25][C@@H:26]3[CH2:30][O:29][C@@H:28]4[C@H:31]([OH:34])[CH2:32][O:33][C@H:27]34)=[N:22][C:5]2=[N:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 90042588HCID 90042588, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 90067422HCID 90067422, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 887MethanolSolvent

Procedure

Placed 4-(4-(6-chloro-2-(((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl)oxy)-1H-imidazo[4,5-b]pyridin-5-yl)phenyl)-3,6-dihydro-2H-thiopyran 1,1-dioxide (5 mg, 0.010 mmol) under nitrogen in methanol (1.0 ml). A few drops of DCM were added to dissolve the solid. Then 10% Pd(C) (10 mg, 9.92 μmol) was added and a slight vacuum was pulled followed by the introduction of hydrogen gas (3×). The reaction mixture was stirred under 1 atmosphere of hydrogen gas at room temperature for 1.5 hours, then filtered and concentrated under reduced pressure. The resulting residue was chromatographed using a 20 g silica gel cartridge eluted with 0-10% methanol in DCM over 10 column volumes. The desired product fractions were combined and concentrated under reduced pressure to provide the title compound as a white solid. LC-MS: calculated for C23H24ClN3O6S 505.09 observed m/e: 505.98 (M+H)+ (Rt 2.58/4 min).

Workup

  1. dissolutionto dissolve the solid
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was chromatographed
  5. washeluted with 0-10% methanol in DCM over 10 column volumes
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2b341a3a59143bcb4d3568a4e716cfa
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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