Ethylamine → 2-[6-(4-chlorophenyl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[3,4-d][1,5]benzodiazepin-4-yl]-N-ethylacetamide

HRID 1485404Notes

Reaction equation

HRID 1485404 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=O)[CH:13]([CH2:16][C:17]([OH:19])=O)[C:12]3=[N:20][N:21]=[C:22]([CH3:23])[N:11]3[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)=[CH:4][CH:3]=1.[CH2:28]([NH2:30])[CH3:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH:13]([CH2:16][C:17]([NH:30][CH2:28][CH3:29])=[O:19])[C:12]3=[N:20][N:21]=[C:22]([CH3:23])[N:11]3[C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 709789952-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetic acid

Product 1

HCID 709791302-[6-(4-chlorophenyl)-1-methyl-4,5-dihydro-[1,2,4]triazolo[3,4-d][1,5]benzodiazepin-4-yl]-N-ethylacetamideYield 25.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetic acid (15 mg, 0.04 mmol), ethanamine (4 mg, 1.12 mmol), HATU (19 mg, 0.05 mmol), DIEA (8 mg, 0.06 mmol) in DCM (5 mL) was stirred overnight at room temperature. The mixture was concentrated and purified by prep-HPLC to give 2-(6-(4-chlorophenyl)-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)-N-ethylacetamide as a white solid (4 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-8c526b261100431b8a8b7de47d75c1be
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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