Hydrochloric Acid → HCID 178458674, compound

HRID 518737Notes

Reaction equation

HRID 518737 reaction equation
[F:1][C:2]1[CH:53]=[CH:52][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:40]=[CH:39][C:38]([CH2:41][N:42]4[CH2:47][CH2:46][CH:45]([C:48]([OH:51])([CH3:50])[CH3:49])[CH2:44][CH2:43]4)=[CH:37][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([N:22]3[CH:27]4[CH2:28][CH2:29][CH:23]3[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26]4)=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.[ClH:54].O1CCOCC1>C(Cl)Cl>[ClH:54].[ClH:54].[CH:23]12[N:22]([C:20]([C@@H:17]3[CH2:18][CH2:19][C@H:14]([N:13]4[C:12]5[CH:37]=[C:38]([CH2:41][N:42]6[CH2:43][CH2:44][CH:45]([C:48]([OH:51])([CH3:50])[CH3:49])[CH2:46][CH2:47]6)[CH:39]=[CH:40][C:11]=5[NH:10]/[C:9]/4=[N:8]\[C:6](=[O:7])[C:5]4[CH:52]=[CH:53][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:15][CH2:16]3)=[O:21])[CH:27]([CH2:28][CH2:29]1)[CH2:26][NH:25][CH2:24]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178451468HCID 178451468, compound

Product 1

HCID 178458674HCID 178458674, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 8-(cis-4-((E)-2-(4-fluorobenzoylimino)-6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarbonyl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (70 mg, 0.096 mmol) in DCM (2 mL) was added 4 M HCl in dioxane (0.120 mL, 0.479 mmol). The suspension was stirred overnight at RT. After 16 hours, the reaction was concentrated to provide (E)-N-(1-(cis-4-(3,8-diazabicyclo[3.2.1]octane-8-carbonyl)cyclohexyl)-6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1H-benzo[d]imidazol-2(3H)-ylidene)-4-fluorobenzamide dihydrochloride as a white powder (68 mg, 101% yield). MS, m/z (C36H47FN6O3.2HCl): calcd, 630.4. found, 631.2 [M+H].

Workup

  1. waitAfter 16 hours
  2. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-8b4b47b36b29456d9828c6c1fc9af481
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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