Diisopropylethylamine → HCID 45137481, compound

HRID 2278742Notes

Reaction equation

HRID 2278742 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]3=[O:20])[CH:11]=[C:10]([C:21](O)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:48][C:49]1[N:54]=[CH:53][C:52]([C@H:55]([NH2:57])[CH3:56])=[CH:51][CH:50]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]3=[O:20])[CH:11]=[C:10]([C:21]([NH:57][C@@H:55]([C:52]3[CH:53]=[N:54][C:49]([CH3:48])=[CH:50][CH:51]=3)[CH3:56])=[O:22])[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58449392HCID 58449392, compoundHCID 67387393HCID 67387393, compound

Product 1

HCID 45137481HCID 45137481, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4′-methyl-5-(2-oxopiperidin-1-yl)biphenyl-3-carboxylic acid (45 mg, 0.14 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (56 mg, 0.29 mmol), 1-hydroxybenzotriazole hydrate (22 mg, 0.14 mmol), and CH2Cl2 (3 mL) were added (R)-1-(6-methylpyridin-3-yl)ethanamine hydrochloride (38 mg, 0.22 mmol) and N,N-diisopropylethylamine (51 μL, 0.29 mmol). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified by preparative HPLC (100×20.2 mm, C18 column; 30-80% CH3CN-water [10 mM Et2NH]) to afford a white foam.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC (100×20.2 mm, C18 column; 30-80% CH3CN-water [10 mM Et2NH])
  3. customto afford a white foam

Sources & evidence

ORD record
ord-5e022b6750b0497fad1ab6ff96ce8235
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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