Hydrochloric Acid → HCID 178502310, compound

HRID 1751352Notes

Reaction equation

HRID 1751352 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:53]([CH3:55])[CH3:54])[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[S:31][C:30]2[CH:32]=[C:33]([C:36]4[NH:40][C:39]([C@@H:41]5[CH2:45][CH2:44][CH2:43][N:42]5C(OC(C)(C)C)=O)=[N:38][CH:37]=4)[CH:34]=[CH:35][C:29]=2[CH:28]=1)=[CH:21][CH:20]=3)=[O:8])=[O:4].Cl.[CH3:57][O:58][C:59]([NH:61][C@H:62]([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:63]([OH:65])=O)=[O:60].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>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:53]([CH3:55])[CH3:54])[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[S:31][C:30]2[CH:32]=[C:33]([C:36]4[NH:40][C:39]([C@@H:41]5[CH2:45][CH2:44][CH2:43][N:42]5[C:63](=[O:65])[C@H:62]([NH:61][C:59](=[O:60])[O:58][CH3:57])[C:66]5[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=5)=[N:38][CH:37]=4)[CH:34]=[CH:35][C:29]=2[CH:28]=1)=[CH:21][CH:20]=3)=[O:8])=[O:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178502311HCID 178502311, compound

Product 1

HCID 178502310HCID 178502310, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-tert-butyl 2-(5-(2-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-naphtho[1,2-d]imidazol-7-yl)benzo[b]thiophen-6-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (53 mg, 0.07 mmol) in DCM (3 mL) was added HCl (4M in dioxane, 0.25 mL). The solution stirred for 1 h, and the solvent was removed. The intermediate was dissolved in DMF (2 mL). (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (15 mg, 0.07 mmol), COMU (36 mg, 0.08 mmol), and DIPEA (0.06 mL, 0.35 mmol) were added sequentially. The solution was stirred o/n and the mixture was purified by HPLC to yield product (14.8 mg). LCMS-ESI+: calc'd for C47H48N8O6S: 853.00 (M+); Found: 853.22 (M+H+).

Workup

  1. customthe solvent was removed
  2. dissolutionThe intermediate was dissolved in DMF (2 mL)
  3. stirringThe solution was stirred o/n and the mixture
  4. customwas purified by HPLC

Sources & evidence

ORD record
ord-77b85dded4ec49dfadcfa27fb517b46f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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