Hydrochloric Acid → HCID 90220939, compound

HRID 1481905Notes

Reaction equation

HRID 1481905 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]=2[CH3:27])[C:12]2[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:11]=2[NH:10][CH2:9]1)(C)(C)C.[ClH:35]>O1CCOCC1>[ClH:35].[NH2:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]=2[CH3:27])[C:12]2[CH:28]=[CH:29][C:30]([C:32]#[N:33])=[CH:31][C:11]=2[NH:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90221188HCID 90221188, compound2×

Product 1

HCID 90220939HCID 90220939, compoundYield 90.15%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of [(S)-7-cyano-1-(2-methyl-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester (Intermediate 9) (400 mg, 0.877 mmol) in 1,4 dioxane (3 mL) at 0° C. was added 4 N HCl in dioxane solution (0.7 mL) dropwise. The mixture was stirred for 16 h at RT. The mixture was concentrated and the residue was triturated with diethyl ether to provide (S)-3-amino-1-(2-methyl-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbonitrile hydrochloride (310 mg, 90.15%) obtained as an off white solid. LC-MS: 357.2 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9886a6c0850341c69f15685fa252cc65
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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