HCID 90136027, compound → HCID 90114269, compound

HRID 2275890Notes

Reaction equation

HRID 2275890 reaction equation
[F:1][C:2]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:18][C:19]34[CH2:25][CH:24]3[CH2:23][CH2:22][N:21](C(OCC3C=CC=CC=3)=O)[CH2:20]4)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1>[Pd]>[C:19]12([NH:18][C:16]([C:12]3[N:8]4[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][C:3]5[C:2]([F:1])=[CH:39][CH:38]=[CH:37][C:36]=5[F:40])[C:7]4=[N:14][C:13]=3[CH3:15])=[O:17])[CH2:25][CH:24]1[CH2:23][CH2:22][NH:21][CH2:20]2

Participants

3

Reactant 1

HCID 90136027HCID 90136027, compound

Product 1

HCID 90114269HCID 90114269, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

216 mg of rac-benzyl 1-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-3-azabicyclo[4.1.0]heptan-3-carboxylate (Example 176A, 0.4 mmol, 1 equivalent) were reacted [0.2 equivalents of palladium on activated carbon (10%), reaction time: 16 h] and worked up analogously to Example 121 [After the separation by HPLC, the residue was taken up in ethyl acetate and washed twice with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated]. This gave 123 mg (74% of theory; 98%) of the title compound.

Workup

  1. customAfter the separation by HPLC
  2. washwashed twice with saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated]

Sources & evidence

ORD record
ord-95183814c4074ad49f39d9f723872c0d
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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