Triethylamine → 1-[(e)-3-(3-Chloro-phenyl)-acryloyl]-4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one

HRID 1867455Notes

Reaction equation

HRID 1867455 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.Cl.Cl.[N:15]1([CH2:21][CH2:22][CH2:23][N:24]2[C:30](=[O:31])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CCN(CC)CC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:27]2[CH2:28][CH2:29][C:30](=[O:31])[N:24]([CH2:23][CH2:22][CH2:21][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:25][CH2:26]2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7352502-Propenoic acid, 3-(3-chlorophenyl)-HCID 670807474-(3-Piperidin-1-yl-propyl)-[1,4]diazepan-5-one dihydrochloride2×

Product 1

HCID 684321561-[(e)-3-(3-Chloro-phenyl)-acryloyl]-4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-oneYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (E)-3-(3-Chloro-phenyl)-acrylic acid acid (26 mg, 0.12 mmol), 4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one-dihydrochloride (intermediate 4) (24 mg, 0.1 mmol), O-(7-azabenotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (46 mg, 0.12 mmol) in DMF (1 ml) was added Et3N (21 ul, 0.15 mmol) and the mixture shaken for 1 h. The reaction was then directly purified by preparative HPLC affording the title product (28 mg, 69%) as a white powder. MS: 404.2 (MH+).

Workup

  1. customThe reaction was then directly purified by preparative HPLC

Sources & evidence

ORD record
ord-128b001c0957498e89d684ed580dccdd
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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