Hydrochloric Acid → HCID 178502314, compound

HRID 1751428Notes

Reaction equation

HRID 1751428 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:34](=[CH:35][CH:36]=1)[CH:33]=[C:32]([C:37]1[NH:41][C:40]([C@@H:42]4[CH2:46][CH2:45][CH2:44][N:43]4[C:47]([O:49]C(C)(C)C)=O)=[N:39][CH:38]=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]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)C(O)=O)=[O:61].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>[CH3:58][O:59][C:60]([NH:62][C@H:63]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:47]([N:43]1[CH2:44][CH2:45][CH2:46][C@H:42]1[C:40]1[NH:41][C:37]([C:32]2[CH:33]=[C:34]3[C:29](=[CH:30][CH:31]=2)[CH:28]=[C:27]([C:22]2[CH:23]=[C:24]4[C:19](=[CH:20][CH:21]=2)[C:17]2[NH:18][C:14]([C@@H:10]5[CH2:11][CH2:12][CH2:13][N:9]5[C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:54]([CH3:55])[CH3:56])=[N:15][C:16]=2[CH:26]=[CH:25]4)[CH:36]=[CH:35]3)=[CH:38][N:39]=1)=[O:49])=[O:61]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178502315HCID 178502315, compound

Product 1

HCID 178502314HCID 178502314, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 2-(5-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-naphtho[1,2-d]imidazol-7-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (88 mg, 0.116 mmol) was dissolved in DCM (5 mL) and HCl (4M in dioxane, 1 mL) was added. After stirring for 1 h, the reaction mixture was concentrated and the residue was treated with (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (24 mg, 0.116 mmol), COMU (50 mg, 0.116 mmol) and DMF (3 mL). DIPEA (0.101 mL, 0.58 mmol) was added and the mixture was stirred for 13 min before being quenched with H2O and purified by HPLC to afford the title compound (61 mg, 62%). MS: (ESI) m/z 847 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. stirringthe mixture was stirred for 13 min
  3. custombefore being quenched with H2O
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-7dcce5bcfd2f4ebd8af9700ba8b27b24
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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