Hydrochloric Acid → HCID 66620099, compound

HRID 71744Notes

Reaction equation

HRID 71744 reaction equation
Cl.C(OC(=O)[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[NH:17][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[NH:34][C:35]([CH:38]6[CH2:42][CH2:41][CH2:40][N:39]6[C:43](=[O:53])[CH:44]([NH:48][C:49]([O:51][CH3:52])=[O:50])[CH:45]([CH3:47])[CH3:46])=[N:36][CH:37]=5)=[CH:29][CH:28]=4)=[CH:23][CH:22]=3)=[CH:19][N:20]=2)[C:10]1=[O:54])(C)(C)C>O1CCOCC1.ClCCl>[CH3:52][O:51][C:49](=[O:50])[NH:48][C@@H:44]([C:43]([N:39]1[CH2:40][CH2:41][CH2:42][CH:38]1[C:35]1[NH:34][C:33]([C:30]2[CH:29]=[CH:28][C:27]([C:24]3[CH:25]=[CH:26][C:21]([C:18]4[NH:17][C:16]([CH2:15][N:11]5[CH2:12][CH2:13][CH2:14][CH:9]([NH2:8])[C:10]5=[O:54])=[N:20][CH:19]=4)=[CH:22][CH:23]=3)=[CH:32][CH:31]=2)=[CH:37][N:36]=1)=[O:53])[CH:45]([CH3:47])[CH3:46]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66620369HCID 66620369, compound

Product 1

HCID 66620099HCID 66620099, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrogen chloride (4N, 8 mL) in dioxane was added to a solution of (R)-{1-[5-(4′-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-ylmethyl]-2-oxo-piperidin-3-yl}-carbamic acid tert-butyl ester (175 mg, 0.24 mmol) in dichloromethane (2 mL). After 1 hour the solvent was removed under reduced pressure. The resulting residue was placed on a high vacuum for 1 hour to provide (R)-{1-[2-(5-{4′-[2-(3-amino-2-oxo-piperidin-1-ylmethyl)-3H-imidazol-4-yl]-biphenyl-4-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester. The yield was assumed to be 100% percent. A sample suitable for analysis was obtained by subjection to reverse phase chromatography with an eluent of 0.1% TFA in water and 0.1% TFA in acetonitrile. The product-containing fractions were combined and the solvent was removed by lyophilization. C35H42N8O4 calculated 638.3 observed [M+1]+ 639.4; rt=1.41 min. 1H (DMSO-d6): δ=8.33 (m, 1H), 8.12 (m, 1H), 7.99 (m, 1H), 7.92 (m, 6H), 7.26 (d, J=8.4 Hz, 1H), 5.13 (t, J=8.0 Hz, 1H), 4.83 (m, 2H), 4.09 (t J=8.0 Hz, 1H), 4.09-3.82 (series m, 6H), 2.36 (m, 2H), 2.14 (m, 2H), 1.96 (m, 4H), 0.76 (m, 6H).

Workup

  1. customAfter 1 hour the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e35c038ab6ab4649bb9dcab0a769b087
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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