tert-Butyl 2-(5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-cyclobutyl-4-methylphenyl)-6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate → 4-(1-(4-Cyclobutyl-2-methyl-5-(4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrile

HRID 541438Notes

Reaction equation

HRID 541438 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:18]([CH3:43])=[CH:19][C:20]([CH:39]4[CH2:42][CH2:41][CH2:40]4)=[C:21]([C:23]4[NH:38][C:26]5[CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][CH2:30][C:25]=5[N:24]=4)[CH:22]=3)=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]>ClCCl.FC(F)(F)C(O)=O.Cl.O>[CH:39]1([C:20]2[C:21]([C:23]3[NH:38][C:26]4[CH2:27][NH:28][CH2:29][CH2:30][C:25]=4[N:24]=3)=[CH:22][C:17]([C:15]([N:12]3[CH2:11][CH2:10][CH:9]([C:6]4[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)[CH2:14][CH2:13]3)=[O:16])=[C:18]([CH3:43])[CH:19]=2)[CH2:40][CH2:41][CH2:42]1

Participants

6

Reactant 1

HCID 68288839tert-Butyl 2-(5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-cyclobutyl-4-methylphenyl)-6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate

Product 1

HCID 682890604-(1-(4-Cyclobutyl-2-methyl-5-(4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-2-yl)benzoyl)piperidin-4-yl)benzonitrileYield 47.1%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-(5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-cyclobutyl-4-methylphenyl)-6,7-dihydro-3H-imidazo[4,5-c]pyridine-5(4H)-carboxylate (406.2, 600 mg, 0.620 mmol, 1.00 equiv, 60%) in dichloromethane (3 mL) and trifluoroacetic acid (1.5 mL) was stirred for 3 h at 25° C., then diluted with 5 mL of hydrochloric acid (3 mol/L) and 10 mL of water. The resulting mixture was washed with 3×20 mL of ethyl acetate and the pH was then adjusted to ˜9 with sodium hydroxide (aq, 3 M). The resulting mixture was extracted with 4×20 mL of dichloromethane. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to yield 140 mg (37%) of the title compound as a brown solid.

Workup

  1. washThe resulting mixture was washed with 3×20 mL of ethyl acetate
  2. extractionThe resulting mixture was extracted with 4×20 mL of dichloromethane
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c13d54f834ad4d36ab63dce3e4981736
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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