Hydrochloric Acid → HCID 178502334, compound

HRID 1751430Notes

Reaction equation

HRID 1751430 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:52]([CH3:54])[CH3:53])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:18][C:17]2[C:19]3[C:24]([CH:25]=[CH:26][C:16]=2[N:15]=1)=[CH:23][C:22]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[NH:37][C:36]([C@@H:38]4[C@@H:43]5[CH2:44][C@@H:40]([CH2:41][CH2:42]5)[N:39]4C(OC(C)(C)C)=O)=[N:35][CH:34]=2)=[CH:29][CH:28]=1)=[CH:21][CH:20]=3)=[O:8])=[O:4].Cl.[CH3:56][O:57][C@H:58]([CH3:68])[C@H:59]([NH:63][C:64]([O:66][CH3:67])=[O:65])[C:60]([OH:62])=O.CCOC(C(C#N)=NOC(N1CCOCC1)=[N+](C)C)=O.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:67][O:66][C:64]([NH:63][C@@H:59]([C@H:58]([O:57][CH3:56])[CH3:68])[C:60]([N:39]1[C@H:38]([C:36]2[NH:37][C:33]([C:30]3[CH:31]=[CH:32][C:27]([C:22]4[CH:23]=[C:24]5[C:19](=[CH:20][CH:21]=4)[C:17]4[NH:18][C:14]([C@@H:10]6[CH2:11][CH2:12][CH2:13][N:9]6[C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:52]([CH3:53])[CH3:54])=[N:15][C:16]=4[CH:26]=[CH:25]5)=[CH:28][CH:29]=3)=[CH:34][N:35]=2)[C@@H:43]2[CH2:44][C@H:40]1[CH2:41][CH2:42]2)=[O:62])=[O:65]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 59540170(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178502335HCID 178502335, compound

Product 1

HCID 178502334HCID 178502334, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(1R,3S,4S)-tert-butyl 3-(5-(4-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-naphtho[1,2-d]imidazol-7-yl)phenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (73 mg, 0.0997 mmol) was dissolved in DCM (5 mL) and treated with HCl (4M in dioxane, 1 mL). After 3 h, the reaction mixture was concentrated. The residue was treated with (2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid (23 mg, 0.120 mmol), COMU (51 mg, 0.120 mmol) and DMF (2 mL). DIPEA (0.090 mL, 0.499 mmol) was added and the reaction mixture was stirred for 25 min before being quenched with H2O and purified by HPLC to afford the title compound (22 mg, 28%). (ESI) m/z 805 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custombefore being quenched with H2O
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-063bd6d12cb34694b86e5509736e2089
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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