Diisopropylethylamine → HCID 44223103, compound

HRID 1845202Notes

Reaction equation

HRID 1845202 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:26])[NH:17][CH2:18][C:19]2[CH:20]=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[CH:13]=[C:12]([C:27](O)=[O:28])[CH:11]=1)#[N:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.[OH:63][CH:64]1[CH2:67][NH:66][CH2:65]1>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:27]([N:66]2[CH2:67][CH:64]([OH:63])[CH2:65]2)=[O:28])[CH:13]=[C:14]([C:16]([NH:17][CH2:18][C:19]2[CH:20]=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=2)=[O:26])[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 67053765HCID 67053765, compound

Product 1

HCID 44223103HCID 44223103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottom flask was charged with 2′-cyano-4′-methyl-5-((6-methylpyridin-3-yl)methylcarbamoyl)biphenyl-3-carboxylic acid (80 mg, 0.24 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (80 mg, 0.42 mmol), 1-hydroxybenzotriazole hydrate (64 mg, 0.42 mmol), N,N-diisopropylethylamine (110 mg, 0.83 mmol), methylene chloride (5 mL) and 3-hydroxyazetidine hydrochloride (45 mg, 0.42 mmol). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified via flash chromatography to afford the desired product as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-c90c2b03ef5342a4ae2d4130010a7bde
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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