Hydrochloric Acid → HCID 178502415, compound

HRID 1751420Notes

Reaction equation

HRID 1751420 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:15][C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[C:24]([C:29]2[CH:30]=[C:31]4[C:51](=[CH:52][CH:53]=2)[C:35]2[NH:36][C:37]([C@@H:39]5[CH2:43][CH2:42][CH2:41][N:40]5C(OC(C)(C)C)=O)=[N:38][C:34]=2[CH2:33][CH2:32]4)[CH:23]=[CH:22]3)=[CH:17][N:18]=1)=[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:64]([OH:66])=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>ClCCl.O.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:64]([N:40]1[CH2:41][CH2:42][CH2:43][C@H:39]1[C:37]1[NH:36][C:35]2[C:51]3[C:31]([CH2:32][CH2:33][C:34]=2[N:38]=1)=[CH:30][C:29]([C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:16]1[NH:15][C:14]([C@@H:10]4[CH2:11][CH2:12][CH2:13][N:9]4[C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:54]([CH3:56])[CH3:55])=[N:18][CH:17]=1)[CH:28]=[CH:27]2)=[CH:53][CH:52]=3)=[O:66])=[O:61]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 75951468(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphateHCID 178502416HCID 178502416, compound

Product 1

HCID 178502415HCID 178502415, compoundYield 64.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 2-(7-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (246 mg, 0.325 mmol) was dissolved in dichloromethane (10 mL) and HCl (4 M in dioxane, 2 mL) was added. After stirring at RT for 1 h 40 min, the reaction mixture was concentrated. The crude residue was treated with (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (75 mg, 0.358 mmol), COMU (139 mg, 0.325 mmol) and DMF (6 mL). DIPEA was added to the stirred reaction mixture dropwise. After 35 min, 1 mL H2O was added and the crude solution was purified by HPLC to afford the title compound (177 mg, 64%). MS (ESI) m/z 849 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. waitAfter 35 min
  3. customthe crude solution was purified by HPLC

Sources & evidence

ORD record
ord-d4851ed6bea54350b88e2b3bdaf97e79
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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