6-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide → 6-[4-(3,3-Difluoro-2-oxo-2,3-dihydroindol-1-YL)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

HRID 552158Notes

Reaction equation

HRID 552158 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.C1(CCCNC(C2N=NC(Cl)=CC=2)=O)CC1.[F:32][C:33]1([F:49])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]([CH:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[C:34]1=[O:48]>>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:45]3[CH2:46][CH2:47][CH:42]([N:35]4[C:36]5[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:33]([F:32])([F:49])[C:34]4=[O:48])[CH2:43][CH2:44]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamideHCID 671722233,3-Difluoro-1-piperidin-4-yl-1,3-dihydroindol-2-oneHCID 860259516-Chloropyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide

Product 1

HCID 117118836-[4-(3,3-Difluoro-2-oxo-2,3-dihydroindol-1-YL)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amideYield 77%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide to replace 6-chloropyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide to react with 3,3-difluoro-1-piperidin-4-yl-1,3-dihydroindol-2-one, the title compound was obtained as a white powder in 77% yield (0.075 g). 1H NMR (300 MHz, CDCl3) δ 8.06 (m, 2H), 7.56-7.53 (m, 1H), 7.42 (t, J=9.0 Hz, 1H), 7.21-7.04 (m, 2H), 6.88 (d, J=6.9 Hz, 1H), 4.73-4.69 (m, 2H), 4.46-4.35 (m, 1H), 3.61-3.52 (m, 2H), 3.17-3.09 (m, 2H), 2.50-2.37 (m, 2H), 1.97-1.93 (m, 2H), 1.59-1.43 (m, 2H), 0.81-0.68 (m, 1H), 0.51-40 (m, 2H), 0.11-0.06 (m, 1H). 13C NMR (75 MHz, CDCl3) δ 165.2, 163.0, 159.6, 145.0, 142.4, 142.3, 133.5, 127.2, 125.2, 123.8, 120.4, 112.6, 110.8, 110.3, 50.9, 44.7, 39.7, 34.5, 27.6, 8.7, 4.2. MS (ES+) m/z 442.2 (M+1).

Sources & evidence

ORD record
ord-9e60e049ad354c9787d01dd6c561d9ad
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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