Hydrochloric Acid → HCID 178457809, compound

HRID 518705Notes

Reaction equation

HRID 518705 reaction equation
[F:1][C:2]1[CH:46]=[CH:45][C:5]([C:6](/[N:8]=[C:9]2/[N:10]([C@H:33]3[CH2:38][CH2:37][C@@H:36]([C:39](=[O:44])[NH:40][CH:41]([CH3:43])[CH3:42])[CH2:35][CH2:34]3)[C:11]3[CH:16]=[C:15]([O:17][CH:18]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH2:20][CH2:19]4)[N:14]=[CH:13][C:12]=3[NH:32]/2)=[O:7])=[CH:4][CH:3]=1.[ClH:47]>O1CCOCC1.Cl>[ClH:47].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](/[N:8]=[C:9]2/[N:10]([C@H:33]3[CH2:38][CH2:37][C@@H:36]([C:39](=[O:44])[NH:40][CH:41]([CH3:43])[CH3:42])[CH2:35][CH2:34]3)[C:11]3[CH:16]=[C:15]([O:17][CH:18]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]4)[N:14]=[CH:13][C:12]=3[NH:32]/2)=[O:7])=[CH:45][CH:46]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178457810HCID 178457810, compound

Product 1

HCID 178457809HCID 178457809, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 2-(4-((E)-2-(4-fluorobenzoylimino)-1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-6-yloxy)piperidin-1-yl)acetate (81 mg, 0.127 mmol) in dioxane (1.2 mL) was added HCl (4N dioxane) (0.127 mL, 0.509 mmol) and 2 drops of concentrated HCl (0.010 mL, 0.127 mmol). The resulting mixture was stirred at RT for 4 hours. The reaction mixture was concentrated and triturated with about 2 mL of dioxane to produce a precipitate. The off-white solid was collected to afford the title compound (70 mg, 89% yield). M/Z calc'd for C30H37FN6O5: 580.28. found 581 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with about 2 mL of dioxane
  3. customto produce a precipitate
  4. customThe off-white solid was collected

Sources & evidence

ORD record
ord-bc861fa04da44159ac76d6871d5da738
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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