1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86696386, compound

HRID 870683Notes

Reaction equation

HRID 870683 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4].[N:24]1([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([N:27]4[CH2:28][CH2:29][N:24]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][CH2:26]4)=[O:20])=[CH:22][CH:23]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86696383HCID 86696383, compound

Product 1

HCID 86696386HCID 86696386, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction of the 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoic acid (124 mg, 0.4 mmol), tert-butyl piperazine-1-carboxylate (82 mg, 0.44 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (84 mg, 0.44 mmol) and dichloromethane (3 mL) was maintained at room temperature overnight. The resulting solution was purified by preparative HPLC (neutral) to afford tert-butyl 4-(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoyl)piperazine-1-carboxylate (89 mg, 47% yield) as a yellow solid: 1H NMR (METHANOL-d4) δ: 8.20-8.39 (m, J=8.3 Hz, 2H), 7.85 (s, 1H), 7.63 (d, J=9.9 Hz, 1H), 7.48-7.56 (m, 2H), 6.66-6.79 (m, 1H), 4.55 (d, J=12.1 Hz, 1H), 3.82 (br. s., 1H), 3.58-3.73 (m, 1H), 3.35-3.45 (m, 4H), 3.26 (br. s., 1H), 3.17 (d, J=15.2 Hz, 1H), 3.10 (br. s., 1H), 1.92-2.15 (m, 1H), 1.90 (br. s., 1H), 1.72 (quin, J=7.4 Hz, 2H), 1.34-1.57 (m, 14H), 1.01 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 479.3 [(M+H)+, calcd for C26H35N6O3 479.3].

Workup

  1. customThe resulting solution was purified by preparative HPLC (neutral)

Sources & evidence

ORD record
ord-0df55dcf897248ad85bdd492e44d9488
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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