Hydrochloric Acid → HCID 178502324, compound

HRID 1751435Notes

Reaction equation

HRID 1751435 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:54]([CH3:56])[CH3:55])[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:28]=[C:29]2[C:51](=[CH:52][CH:53]=1)[C:33]1[NH:34][C:35]([C@@H:37]4[C@@H:42]5[CH2:43][C@@H:39](CC5)[N:38]4C(OC(C)(C)C)=O)=[N:36][C:32]=1[CH:31]=[CH:30]2)=[CH:21][CH:20]=3)=[O:8])=[O:4].Cl.[CH3:58][O:59][C:60]([NH:62][C@@H:63]([CH:67]([CH3:69])[CH3:68])[C:64](O)=[O:65])=[O:61].[CH3:70][CH2:71]OC(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>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:54]([CH3:56])[CH3:55])[C:7]([N:9]1[C@H:10]([C:14]2[NH:18][C:17]3[C:19]4[C:24]([CH:25]=[CH:26][C:16]=3[N:15]=2)=[CH:23][C:22]([C:27]2[CH:28]=[C:29]3[C:51](=[CH:52][CH:53]=2)[C:33]2[NH:34][C:35]([C@@H:37]5[CH2:42][CH2:43][CH2:39][N:38]5[C:64](=[O:65])[C@@H:63]([NH:62][C:60](=[O:61])[O:59][CH3:58])[CH:67]([CH3:69])[CH3:68])=[N:36][C:32]=2[CH:31]=[CH:30]3)=[CH:21][CH:20]=4)[C@@H:11]2[CH2:12][C@H:13]1[CH2:70][CH2:71]2)=[O:8])=[O:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178502326HCID 178502326, compound

Product 1

HCID 178502324HCID 178502324, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(1R,3S,4S)-tert-butyl 3-(2′-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (102 mg, 0.135 mmol) was dissolved in DCM (5 mL) and treated with HCl (4M in dioxane, 1 mL). After 2 h, the reaction mixture was concentrated. The residue was treated with (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (28 mg, 0.149 mmol), COMU (58 mg, 0.135 mmol) and DMF (3 mL). DIPEA (0.12 mL, 0.675 mmol) was added and the reaction mixture was stirred for 1.5 h before being quenched with H2O and purified by HPLC to afford the title compound (86 mg, 77%). (ESI) m/z 814 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-db96ba0e44654a6b89690fc3dc36936f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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