1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86696384, compound

HRID 870681Notes

Reaction equation

HRID 870681 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].[NH:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:26][CH2:25]1.C(N=C=NCCCN(C)C)C>ClCCl>[C:33]([O:32][C:31](=[O:37])[NH:30][CH:27]1[CH2:26][CH2:25][N:24]([C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([C:12]3[N:10]4[N:11]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=[CH:8][C:9]4=[N:14][CH:13]=3)=[CH:23][CH:22]=2)[CH2:29][CH2:28]1)([CH3:34])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 7238334-(N-Boc-amino)piperidineHCID 86696383HCID 86696383, compound

Product 1

HCID 86696384HCID 86696384, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction of the 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoic acid (93 mg, 0.3 mmol), tert-butyl piperidin-4-ylcarbamate (66 mg, 0.33 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (63 mg, 0.33 mmol) and dichloromethane (3 mL) was maintained at room temperature overnight. The resulting solution was purified by preparative HPLC (neutral) to afford tert-butyl(1-(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoyl)piperidin-4-yl)carbamate (76 mg, 52% yield) as a yellow solid: 1H NMR (METHANOL-d4) δ: 8.23-8.43 (m, J=8.3 Hz, 2H), 7.85 (s, 1H), 7.63 (d, J=9.9 Hz, 1H), 7.45-7.56 (m, 2H), 6.68-6.87 (m, 1H), 4.55 (d, J=12.1 Hz, 1H), 3.82 (br. s., 1H), 3.59-3.72 (m, 1H), 3.35-3.48 (m, 4H), 3.19 (d, J=15.2 Hz, 2H), 1.92-2.17 (m, 1H), 1.90 (br. s., 1H), 1.72 (m, 2H), 1.35-1.59 (m, 13H), 1.01 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 493.3 [(M+H)+, calcd for C27H37N6O3 493.3].

Workup

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

Sources & evidence

ORD record
ord-d51bae09472d40eeb0ebcd7c8acfc67e
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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