Hydrochloric Acid → HCID 73427079, compound

HRID 1486065Notes

Reaction equation

HRID 1486065 reaction equation
[C:1]([N:4]1[C@@H:10]([CH3:11])[C@H:9]([NH:12][C:13](=[O:25])[C@@H:14]([N:16](C)[C:17](=O)OC(C)(C)C)[CH3:15])[C:8](=[O:26])[N:7]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[CH:30][C:29]=2[CH3:38])[C:6]2[CH:39]=[CH:40][CH:41]=[CH:42][C:5]1=2)(=[O:3])[CH3:2].[ClH:43]>O1CCOCC1.CCOCC>[ClH:43].[ClH:43].[C:1]([N:4]1[C@@H:10]([CH3:11])[C@H:9]([NH:12][C:13](=[O:25])[C@@H:14]([NH:16][CH3:17])[CH3:15])[C:8](=[O:26])[N:7]([CH2:27][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]=[CH:30][C:29]=2[CH3:38])[C:6]2[CH:39]=[CH:40][CH:41]=[CH:42][C:5]1=2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118292680HCID 118292680, compound

Product 1

HCID 73427079HCID 73427079, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(S)-1-((2S,3S)-1-acetyl-2-methyl-5-((3-methylquinolin-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (96 mg, 167 μmol) in 4 M HCl in dioxane (837 μl) was stirred for 1.5 h. The reaction was diluted with Et2O and the solids were collected by vacuum filtration, taken up in MeCN—H2O, and lyophilized to provide (S)-N-((2S,3S)-1-acetyl-2-methyl-5-((3-methylquinolin-4-yl)methyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide dihydrochloride (72.2 mg, 79%) as an off-white solid. MS m/z 474 (MH)+.

Workup

  1. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-2beb5caf092f413a89d9c3480c92e334
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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