Diisopropylethylamine → HCID 131726276, compound

HRID 351181Notes

Reaction equation

HRID 351181 reaction equation
C(OC([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1)=O)(C)(C)C.C([N:38](CC)[CH:39]([CH3:41])[CH3:40])(C)C.[OH2:44].[OH:45]N1C2C=CC=CC=2N=N1.Cl.C[N:57]([CH3:66])CCCN=C=NCC>ClCCCl>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)[C:40](=[O:45])[C@H:39]([CH2:41][C:66]([NH2:57])=[O:44])[NH2:38])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22018600N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 131726276HCID 131726276, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (420 mg, 0.92 mmol) and N -(tert-butoxycarbonyl)-L-aspartic acid β-t-butyl ester (305 mg, 1.06 mmol) in 1,2-dichloroethane (6 mL) was added N,N-diisopropylethylamine (0.50 mL, 2.88 mmol), 1-hydroxybenzotriazole hydrate (175 mg, 1.30 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (EDC) (250 mg, 1.30 mmol) and the reaction mixture was stirred at room temperature for 18 hours. The reaction was worked-up as described above and the crude material was purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2) to give the desired amide (145 mg, 23%) as a mixture of diastereomers.

Workup

  1. customwas purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2)

Sources & evidence

ORD record
ord-e1d74e3fac204e0e98b0175c13427937
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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