Hydrochloric Acid → (3S,4S)-3-amino-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]diazepine-7-carbonitrile dihydrochloride

HRID 1486126Notes

Reaction equation

HRID 1486126 reaction equation
[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[N:7]([CH2:30][C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=[CH:33][C:32]=3[CH:41]3[CH2:43][CH2:42]3)[C:8](=[O:29])[C@@H:9]([NH:21]C(=O)OC(C)(C)C)[C@H:10]([CH3:20])[N:11]([C:12]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])[C:5]=2[CH:4]=1)#[N:2].[ClH:46]>O1CCOCC1.CCOCC>[ClH:46].[ClH:46].[NH2:21][C@@H:9]1[C:8](=[O:29])[N:7]([CH2:30][C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[CH:33][C:32]=2[CH:41]2[CH2:43][CH2:42]2)[C:6]2[CH:44]=[CH:45][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:11]([C:12]([CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])[C@H:10]1[CH3:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118292724tert-butyl(3S,4S)-7-cyano-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-ylcarbamate

Product 1

HCID 90082427(3S,4S)-3-amino-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]diazepine-7-carbonitrile dihydrochlorideYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(3S,4S)-7-cyano-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-ylcarbamate (69 mg, 113 μmol) in 4 M HCl in dioxane (566 μl) was stirred for 2 h. The reaction was diluted with Et2O and the solids were collected by vacuum filtration to provide (3S,4S)-3-amino-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]diazepine-7-carbonitrile dihydrochloride (60 mg, 91%) as a white solid.

Workup

  1. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-f304442355434e27a263e9815c9ca3f7
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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