Hydrochloric Acid → (S)-N-((3S,4S)-7-cyano-4-methyl-1-((2-methylnaphthalen-1-yl)methyl)-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)butanamide hydrochloride

HRID 1486102Notes

Reaction equation

HRID 1486102 reaction equation
[C:1]([C:3]1[CH:49]=[CH:48][C:6]2[N:7]([CH2:36][C:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=[CH:39][C:38]=3[CH3:47])[C:8](=[O:35])[C@@H:9]([NH:20][C:21](=[O:34])[C@@H:22]([N:25](C)[C:26](=O)OC(C)(C)C)[CH2:23][CH3:24])[C@H:10]([CH3:19])[N:11]([C:12](=[O:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:5]=2[CH:4]=1)#[N:2].[ClH:50]>O1CCOCC1.CCOCC>[ClH:50].[C:1]([C:3]1[CH:49]=[CH:48][C:6]2[N:7]([CH2:36][C:37]3[C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=[CH:39][C:38]=3[CH3:47])[C:8](=[O:35])[C@@H:9]([NH:20][C:21](=[O:34])[C@@H:22]([NH:25][CH3:26])[CH2:23][CH3:24])[C@H:10]([CH3:19])[N:11]([C:12](=[O:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118292703HCID 118292703, compound

Product 1

HCID 73425761(S)-N-((3S,4S)-7-cyano-4-methyl-1-((2-methylnaphthalen-1-yl)methyl)-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)butanamide hydrochlorideYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(S)-1-((3S,4S)-7-cyano-4-methyl-1-((2-methylnaphthalen-1-yl)methyl)-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxobutan-2-yl(methyl)carbamate (117 mg, 170 μmol) in 4 M HCl in dioxane (848 μl) was stirred for 1 h. The reaction was diluted with Et2O and the resulting solids were collected by vacuum filtration, taken up in MeCN—H2O, and lyophilized to provide (S)-N-((3S,4S)-7-cyano-4-methyl-1-((2-methylnaphthalen-1-yl)methyl)-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)butanamide hydrochloride (90.5 mg, 85%) as a white solid. MS m/z 590 (MH)+.

Workup

  1. filtrationthe resulting solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-7da321c64c4c48f495f02a475b027bc6
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

Loading…