Hydrochloric Acid → (S)-N-((3S,4S)-1-((1-(2-cyanophenyl)-1H-indazol-3-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 1486073Notes

Reaction equation

HRID 1486073 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:18][N:19]2[C:25](=[O:26])[C@@H:24]([NH:27][C:28](=[O:40])[C@@H:29]([N:31](C)[C:32](=O)OC(C)(C)C)[CH3:30])[C@H:23]([CH3:41])[N:22]([C:42]([CH:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[O:43])[C:21]3[CH:50]=[CH:51][CH:52]=[CH:53][C:20]2=3)=[N:10]1)#[N:2].[ClH:54]>O1CCOCC1.CCOCC>[ClH:54].[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:18][N:19]2[C:25](=[O:26])[C@@H:24]([NH:27][C:28](=[O:40])[C@@H:29]([NH:31][CH3:32])[CH3:30])[C@H:23]([CH3:41])[N:22]([C:42]([CH:44]3[CH2:45][CH2:46][O:47][CH2:48][CH2:49]3)=[O:43])[C:21]3[CH:50]=[CH:51][CH:52]=[CH:53][C:20]2=3)=[N:10]1)#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118292583tert-butyl(S)-1-((3S,4S)-1-((1-(2-cyanophenyl)-1H-indazol-3-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

Product 1

HCID 90082359(S)-N-((3S,4S)-1-((1-(2-cyanophenyl)-1H-indazol-3-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 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(S)-1-((3S,4S)-1-((1-(2-cyanophenyl)-1H-indazol-3-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 (128 mg, 178 μmol) in 4 M HCl in dioxane (889 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-((1-(2-cyanophenyl)-1H-indazol-3-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 (94.1 mg, 81%) as an off-white solid. MS m/z 620 (MH)+.

Workup

  1. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-6f36653e56644b78a16a4820735bb3fa
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

Loading…