Dimethylformamide → Diisopropylethylamine

HRID 917345Notes

Reaction equation

HRID 917345 reaction equation
O[N:2]1[C:6]2[CH:7]=CC=C[C:5]=2N=N1.C(N([CH2:16][CH3:17])CC)C.CN(C)C=O.O1C[CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[CH:25]([N:2]([CH:6]([CH3:5])[CH3:7])[CH2:16][CH3:17])([CH3:26])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The amine 8 may be coupled to a carboxylic acid using 1-ethyl-3-(3-dimethylainopropyl)carbodiimide (EDC), 1-hydroxybenztriazole (HOBT), and a base, generally triethylamine or diisopropylethylamine (DIPEA), in a solvent such as N,N-dimethylformamide (DMF), tetrahydrofuran (THF), or methylene chloride for 3 to 48 hours at ambient temperature to provide intermediate 10.

Sources & evidence

ORD record
ord-af883398386d4ab4ace534c64f2c3a94
Source dataset
uspto-grants-2007_09
Patent number
US07273876B2

Reaction notes

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