Diisopropylethylamine → HCID 58188182, compound

HRID 1845200Notes

Reaction equation

HRID 1845200 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[C:12]([C:21](O)=[O:22])[CH:11]=1)#[N:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[OH:48][CH:49]1[CH2:52][NH:51][CH2:50]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([C:21]([N:51]2[CH2:52][CH:49]([OH:48])[CH2:50]2)=[O:22])[CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:15]=1)#[N:2]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27592903-Hydroxyazetidine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58188306HCID 58188306, compound

Product 1

HCID 58188182HCID 58188182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2′-cyano-5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (90 mg, 0.29 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (120 mg, 0.61 mmol), 1-hydroxybenzotriazole hydrate (93 mg, 0.61 mmol), and methylene chloride (5 mL) were added 3-hydroxyazetidine hydrochloride (67 mg, 0.61 mmol) and N,N-diisopropylethylamine (0.21 mL, 1.2 mmol). The mixture was stirred at room temperature overnight, and then concentrated under reduced pressure. The residue was purified via flash chromatography to afford the desired product as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-033afeadab3441348b5c957490b878c1
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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