Hydrochloric Acid → HCID 73425874, compound

HRID 1486132Notes

Reaction equation

HRID 1486132 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[CH:29]=[C:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])[CH:31]=[CH:32][C:33]=2[O:34][CH3:35])[C:6]2[CH:43]=[CH:44][C:45]([C:47]#[N:48])=[CH:46][C:5]1=2)(=[O:3])[CH3:2].[ClH:49]>O1CCOCC1.CCOCC>[ClH:49].[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[CH:29]=[C:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[F:42])[CH:31]=[CH:32][C:33]=2[O:34][CH3:35])[C:6]2[CH:43]=[CH:44][C:45]([C:47]#[N:48])=[CH:46][C:5]1=2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118292596HCID 118292596, compound

Product 1

HCID 73425874HCID 73425874, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A rt solution of tert-butyl(S)-1-((3S,4S)-5-acetyl-7-cyano-1-((2′-fluoro-4-methoxybiphenyl-3-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (39 mg, 59.3 μmol) in 4 M HCl in dioxane (296 μl) was stirred for 1 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)-5-acetyl-7-cyano-1-((2′-fluoro-4-methoxybiphenyl-3-yl)methyl)-4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide hydrochloride (23.9 mg, 68%) as a white solid. MS m/z 558 (MH)+.

Workup

  1. filtrationthe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-3ee09c26b56b48ccbdb17045e85dc1ae
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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