Hydrochloric Acid → HCID 178457826, compound

HRID 518648Notes

Reaction equation

HRID 518648 reaction equation
C([NH:4][C:5]1[N:6]([C@@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)[C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[N:10]=[CH:9][C:8]=2[N:22]=1)(=[O:3])C.Cl.CO>C(Cl)Cl>[NH4+:4].[OH-:3].[NH2:4][C:5]1[N:6]([C@@H:23]2[CH2:24][CH2:25][C@H:26]([C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]2)[C:7]2[CH:12]=[C:11]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[N:10]=[CH:9][C:8]=2[N:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178474402HCID 178474402, compound

Product 2

HCID 14923Ammonium HydroxideHCID 178457826HCID 178457826, compoundYield 163.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

cis-4-(2-Acetamido-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-1-yl)-N-isopropylcyclohexanecarboxamide (8.56 g, 18.19 mmol) was diluted with 2N HCl (aq) (91 mL, 182 mmol) and heated at 50° C. overnight. The reaction mixture was concentrated in vacuo, and purified via silica gel chromatography using 0-100% 90:10:1 DCM:MeOH:NH4OH in DCM to yield cis-4-(2-amino-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-1-yl)-N-isopropylcyclohexanecarboxamide (6.39 g, 82% yield). MS m/z=429.2 [M+H], calc 428.57 for C23H36N6O2.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-57927f6d1c3a4c768244b46468bee37b
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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