1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66849178, compound

HRID 2424440Notes

Reaction equation

HRID 2424440 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:57]([O:64][CH2:65][C:66](O)=[O:67])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>ClCCl>[CH2:57]([O:64][CH2:65][C:66]([NH:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:15])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1)=[O:67])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 290301(Benzyloxy)acetic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 66849178HCID 66849178, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(6-aminopyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone (1.30 g, 3.7 mmol) in dichloromethane (60 mL) was added diisopropylethylamine (1.5 g), followed by 1-hydroxybenzotriazole monohydrate (1.1 g) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (2 mL). The resulting mixture was stirred for 15 minutes and then benzyloxyacetic acid (1.2 mL) was added. After stirring for 2 hours the reaction mixture was washed with 10% HCl, 1 N NaOH and water, dried over anhydrous Na2SO4 and concentrated in vacuo to afford the final amide as a dark yellow oil. The oil was purified by column chromatography (dichloromethane:MeOH=98:2) providing 1.64 g of pure final compound as a white solid in 89% yield. 1H NMR (300 MHz, CDCl3) δ 9.12, 8.29, 7.72, 7.63-7.49, 7.35-7.33, 6.99, 4.65, 4.10, 4.05-3.83, 3.66-3.54, 3.33-3.29. MS (ES+) m/z 500.2 (M+1).

Workup

  1. stirringAfter stirring for 2 hours the reaction mixture
  2. washwas washed with 10% HCl, 1 N NaOH and water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71acec0f8cc1403a84c7a50bd62e5559
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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