Hydrochloric Acid → (3S,4S)-3-amino-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile dihydrochloride

HRID 1486118Notes

Reaction equation

HRID 1486118 reaction equation
[C:1]([C:3]1[CH:37]=[CH:36][C:6]2[N:7]([CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[CH:25][C:24]=3[CH:33]3[CH2:35][CH2:34]3)[C:8](=[O:21])[C@@H:9]([NH:13]C(=O)OC(C)(C)C)[C@H:10]([CH3:12])[NH:11][C:5]=2[CH:4]=1)#[N:2].[ClH:38]>O1CCOCC1.CCOCC>[ClH:38].[ClH:38].[NH2:13][C@@H:9]1[C:8](=[O:21])[N:7]([CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][C:24]=2[CH:33]2[CH2:35][CH2:34]2)[C:6]2[CH:36]=[CH:37][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[NH:11][C@H:10]1[CH3:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131736782tert-butyl(3S,4S)-7-cyano-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

Product 1

HCID 90082583(3S,4S)-3-amino-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt suspension of tert-butyl(3S,4S)-7-cyano-1-((3-cyclopropylquinolin-4-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (134 mg, 269 μmol) in 4 M HCl in dioxane (1.35 ml) was stirred for 2.5 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-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile dihydrochloride (127 mg, quant.) as an off-white solid. MS m/z 398 (MH)+.

Workup

  1. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-ee41c862928b4180b7ee4a29bca79928
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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