Hydrochloric Acid → (S)-N-((3S,4S)-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide hydrochloride

HRID 1486071Notes

Reaction equation

HRID 1486071 reaction equation
[CH:1]1([C:4]2[CH:5]=[N:6][C:7]3[C:12]([C:13]=2[CH2:14][N:15]2[C:21](=[O:22])[C@@H:20]([NH:23][C:24](=[O:36])[C@@H:25]([N:27](C)[C:28](=O)OC(C)(C)C)[CH3:26])[C@H:19]([CH3:37])[N:18]([C:38]([CH:40]4[CH2:45][CH2:44][O:43][CH2:42][CH2:41]4)=[O:39])[C:17]4[CH:46]=[CH:47][CH:48]=[CH:49][C:16]2=4)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:3][CH2:2]1.[ClH:50]>O1CCOCC1.CCOCC>[ClH:50].[CH:1]1([C:4]2[CH:5]=[N:6][C:7]3[C:12]([C:13]=2[CH2:14][N:15]2[C:21](=[O:22])[C@@H:20]([NH:23][C:24](=[O:36])[C@@H:25]([NH:27][CH3:28])[CH3:26])[C@H:19]([CH3:37])[N:18]([C:38]([CH:40]4[CH2:41][CH2:42][O:43][CH2:44][CH2:45]4)=[O:39])[C:17]4[CH:46]=[CH:47][CH:48]=[CH:49][C:16]2=4)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118292684tert-butyl(S)-1-((3S,4S)-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-ox opropan-2-yl(methyl)carbamate

Product 1

HCID 90082670(S)-N-((3S,4S)-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(S)-1-((3S,4S)-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (78 mg, 116 μmol) in 4 M HCl in dioxane (582 μl) was stirred for 2 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-((3S,4S)-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide hydrochloride (66.8 mg, 95%) as an off-white solid. MS m/z 570 (MH)+.

Workup

  1. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-9a622a40054d415d9dfb2859fd2f76c1
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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