1,4-Dioxane → HCID 89704970, compound

HRID 528685Notes

Reaction equation

HRID 528685 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([C:17](O)=[O:18])=[CH:10][CH:11]=[N:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC1[C:29]2[N:28]=N[NH:26][C:25]=2[CH:24]=[CH:23][CH:22]=1.Cl.[CH2:31]([N:33]=C=NCCCN(C)C)[CH3:32].CCN(C(C)C)C(C)C.[O:51]1CCOCC1>C(Cl)Cl>[C:29]([C@@H:25]1[CH2:24][CH2:23][CH2:22][N:26]1[C:32](=[O:51])[CH2:31][NH:33][C:17]([C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[CH:16][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:12]=[CH:11][CH:10]=1)=[O:18])#[N:28]

Participants

7

Reactant 5

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131735607HCID 131735607, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 89704970HCID 89704970, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing this acid 5-phenylquinoline-4-carboxylic acid (0.04 g, 0.160 mmol) and HOBT (Hydroxybenzotriazole) (0.027 g, 0.177 mmol) in 1,4-dioxane (5 mL) was added a solution of EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide HCl) (0.034 g, 0.177 mmol) in CH2Cl2 (5 mL). The mixture was stirred for 10 min at room temperature. To the resulting solution was added the appropriate amine (S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile 4-methylbenzenesulfonate (0.063 g, 0.193 mmol) and DIPEA (0.059 ml, 0.337 mmol) in CH2Cl2 (4 mL), with stirring.

Workup

  1. stirringwith stirring

Sources & evidence

ORD record
ord-f4beba79145449449d5b0dd94f9d9a55
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

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