Hydrochloric Acid → HCID 178461564, compound

HRID 518623Notes

Reaction equation

HRID 518623 reaction equation
[C:1]([C:3]1[CH:51]=[CH:50][C:6]([C:7](/[N:9]=[C:10]2/[N:11]([C@@H:28]3[CH2:33][CH2:32][C@H:31]([C:34]([N:36]4[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][C@H:37]4[CH3:49])=[O:35])[CH2:30][CH2:29]3)[C:12]3[CH:17]=[C:16]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[N:15]=[CH:14][C:13]=3[NH:27]/2)=[O:8])=[CH:5][CH:4]=1)#[N:2].Cl>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7](/[N:9]=[C:10]2/[N:11]([C@H:28]3[CH2:29][CH2:30][C@@H:31]([C:34]([N:36]4[CH2:41][CH2:40][NH:39][CH2:38][C@H:37]4[CH3:49])=[O:35])[CH2:32][CH2:33]3)[C:12]3[CH:17]=[C:16]([O:18][CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)[N:15]=[CH:14][C:13]=3[NH:27]/2)=[O:8])=[CH:50][CH:51]=1)#[N:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178461582HCID 178461582, compound

Product 1

HCID 178461564HCID 178461564, compoundYield 16.7%

Procedure

A suspension of (R)-tert-butyl 4-(cis-4-((E)-2-(4-cyanobenzoylimino)-6-(2-(piperidin-1-yl)ethoxy)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)cyclohexanecarbonyl)-3-methylpiperazine-1-carboxylate (0.07 g, 0.100 mmol) in HCl (4M in dioxanes) (1.252 mL, 5.01 mmol) was stirred at RT for 16 hours. The mixture was concentrated under reduced pressure, and the residue was suspended in DCM (20 mL) and washed with aqueous NaHCO3 solution (10 mL). The organic layer was collected, dried over sodium sulfate and concentrated to afford a brown solid. This material was purified by silica gel chromatography to afford (E)-4-cyano-N-(1-(cis-4-((R)-2-methylpiperazine-1-carbonyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide (10 mg, 16.7% yield). MS m/z=599.4 [M+H]. Calc'd for C33H42N8O3: 598.3.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washwashed with aqueous NaHCO3 solution (10 mL)
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford a brown solid
  7. customThis material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-327be2e3f46e4374971537c492f6d854
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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