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Ethylamine hydrochloride → N-(((1S,2S)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin]-2-yl)methyl)ethanamine

HRID 1772342
Notes
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Reaction equation

HRID 1772342 reaction equation
Br[CH2:2][C@H:3]1[C@@:5]2([N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:9]3[C:19]([CH3:23])=[C:20]([CH3:22])[S:21][C:8]=3[N:7]3[C:24]([CH3:27])=[N:25][N:26]=[C:6]23)[CH2:4]1.Cl.[CH2:29]([NH2:31])[CH3:30].CCN(C(C)C)C(C)C>CN(C)C=O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:9]3[C:19]([CH3:23])=[C:20]([CH3:22])[S:21][C:8]=3[N:7]3[C:24]([CH3:27])=[N:25][N:26]=[C:6]3[C@@:5]3([CH2:4][C@H:3]3[CH2:2][NH:31][CH2:29][CH3:30])[N:11]=2)=[CH:13][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 57404762(1S,2R)-2-(bromomethyl)-4'-(4-chlorophenyl)-2',3',9'-trimethylspiro-[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

Product 1

HCID 57404938N-(((1S,2S)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin]-2-yl)methyl)ethanamineYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S,2R)-2-(bromomethyl)-4′-(4-chlorophenyl)-2′,3′,9′-trimethylspiro-[cyclopropane-1,6′-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine](50 mg, 0.108 mmol) in anhydrous N,N-dimethylformamide (3 mL) were added ethanamine hydrochloride (221 mg, 2.71 mmol) and Hunig's base (473 μl, 2.71 mmol) at rt. After 4 days at rt, silica gel was added to the reaction, and the solvent was removed under vacuum. The dry silica gel was packed and the product was purified by chromatography (Hexane/EtOAc 5:5 to 0:10 then DCM/MeOH 10:0 to 9:1). A second chromatography was performed (2-propanol 100% then DCM/MeOH 9:1) to give a tan solid (32 mg). LRMS (M+H)+: 426 m/z.

Workup

  1. additionsilica gel was added to the reaction
  2. customthe solvent was removed under vacuum
  3. customthe product was purified by chromatography (Hexane/EtOAc 5:5 to 0:10

Sources & evidence

ORD record
ord-50efbde953d24569aa7920e394fb8d78
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249161B2

Reaction notes

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