Hydrochloric Acid → (1-(6-[5-(4-{6-[2-(4-Cyano-pyrrolidin-2-yl)-3H-imidazol-4-yl]-naphthalen-2-yl}-phenyl)-1H-imidazol-2-yl]-5-aza-spiro[2.4]heptane-5-carbonyl)-2-methyl-propyl)-carbamic acid methyl ester-tris-hydrochloride

HRID 79919Notes

Reaction equation

HRID 79919 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([C:13]#[N:14])[CH2:10][CH:9]1[C:15]1[NH:16][C:17]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[NH:37][C:38]([CH:41]6[CH2:47][C:44]7([CH2:46][CH2:45]7)[CH2:43][N:42]6[C:48](=[O:58])[CH:49]([NH:53][C:54]([O:56][CH3:57])=[O:55])[CH:50]([CH3:52])[CH3:51])=[N:39][CH:40]=5)=[CH:32][CH:31]=4)[CH:26]=3)[CH:21]=2)=[CH:18][N:19]=1)=O)(C)(C)C.[ClH:59].O1CCOCC1>C(Cl)Cl>[ClH:59].[ClH:59].[ClH:59].[CH3:57][O:56][C:54](=[O:55])[NH:53][CH:49]([C:48]([N:42]1[CH:41]([C:38]2[NH:37][C:36]([C:33]3[CH:32]=[CH:31][C:30]([C:25]4[CH:24]=[CH:23][C:22]5[C:27](=[CH:28][CH:29]=[C:20]([C:17]6[NH:16][C:15]([CH:9]7[CH2:10][CH:11]([C:13]#[N:14])[CH2:12][NH:8]7)=[N:19][CH:18]=6)[CH:21]=5)[CH:26]=4)=[CH:35][CH:34]=3)=[CH:40][N:39]=2)[CH2:47][C:44]2([CH2:45][CH2:46]2)[CH2:43]1)=[O:58])[CH:50]([CH3:52])[CH3:51]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 666211324-Cyano-2-{5-[6-(4-{2-[5-(2-methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66620626(1-(6-[5-(4-{6-[2-(4-Cyano-pyrrolidin-2-yl)-3H-imidazol-4-yl]-naphthalen-2-yl}-phenyl)-1H-imidazol-2-yl]-5-aza-spiro[2.4]heptane-5-carbonyl)-2-methyl-propyl)-carbamic acid methyl ester-tris-hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Cyano-2-{5-[6-(4-{2-[5-(2-methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (639 mg, 0.816 mmol) was dissolved in DCM (8 mL) and 4.0 M HCl in dioxane (2 mL, 8 mmol) was added. After stirring for 37 min, the solid was filtered off and rinsed with EtOAc, affording the title compound (597 mg, 92%).

Workup

  1. filtrationthe solid was filtered off
  2. washrinsed with EtOAc

Sources & evidence

ORD record
ord-7319e19538274355bccb2c39cd428419
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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