Hydrochloric Acid → HCID 178502348, compound

HRID 1751425Notes

Reaction equation

HRID 1751425 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1)[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]([CH2:25][CH2:26][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]4C(OC(C)(C)C)=O)=[N:39][CH:38]=1)[CH:31]=[CH:30]2)=[CH:21][CH:20]=3)=[O:8])=[O:4].Cl.[CH3:61][O:62][C:63]([NH:65][C@H:66]([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[C:67]([OH:69])=O)=[O:64].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>[CH3:61][O:62][C:63]([NH:65][C@H:66]([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[C:67]([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]5[CH2:55][CH2:56][O:57][CH2:58][CH2:59]5)=[N:15][C:16]=2[CH2:26][CH2:25]4)[CH:36]=[CH:35]3)=[CH:38][N:39]=1)=[O:69])=[O:64]

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 178502349HCID 178502349, compound

Product 1

HCID 178502348HCID 178502348, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-tert-butyl 2-(5-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetyl)pyrrolidin-2-yl)-4,5-dihydro-1H-naphtho[1,2-d]imidazol-7-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (136 mg, 0.17 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 (36 mg, 0.170 mmol), COMU (73 mg, 0.170 mmol) and DMF (3 mL). DIPEA (0.12 mL, 0.68 mmol) was added dropwise. After 20 min, the reaction was quenched by addition of H2O and the crude mixture was purified by HPLC to afford the title compound (57 mg, 38%). MS: (ESI) m/z 891 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. waitAfter 20 min
  3. customthe reaction was quenched by addition of H2O
  4. customthe crude mixture was purified by HPLC

Sources & evidence

ORD record
ord-0bdb48d9e2234cff8d5be3d7b836abcc
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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