6-Chloro-2-methyl-4-(5-(1-methylpiperidin-4-yl)pyridin-2-ylamino)pyridazin-3(2H)-one → 6-tert-butyl-2-{3-hydroxymethyl-4-[1-methyl-5-(5-methyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydro-pyridazin-3-yl]-pyridin-2-yl}-2H-phthalazin-1-one

HRID 337304Notes

Reaction equation

HRID 337304 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14](C3CCN(C)CC3)=C[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.[C:24]([C:28]1[CH:29]=[C:30]2[C:35](=[C:36](F)[CH:37]=1)[C:34](=[O:39])[N:33]([C:40]1[N:47]=[CH:46][CH:45]=[C:44](I)[C:41]=1[CH:42]=[O:43])[N:32]=[CH:31]2)([CH3:27])([CH3:26])[CH3:25]>>[C:24]([C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[C:34](=[O:39])[N:33]([C:40]1[C:41]([CH2:42][OH:43])=[C:44]([C:2]3[CH:3]=[C:4]([NH:10][C:11]4[CH:16]=[C:15]5[CH2:14][N:6]([CH3:8])[CH2:5][CH2:4][N:10]5[N:12]=4)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=3)[CH:45]=[CH:46][N:47]=1)[N:32]=[CH:31]2)([CH3:27])([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 667423806-Chloro-2-methyl-4-(5-(1-methylpiperidin-4-yl)pyridin-2-ylamino)pyridazin-3(2H)-oneHCID 866737152-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-iodonicotinaldehyde

Product 1

HCID 712579796-tert-butyl-2-{3-hydroxymethyl-4-[1-methyl-5-(5-methyl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydro-pyridazin-3-yl]-pyridin-2-yl}-2H-phthalazin-1-one

Procedure

Preparation by a similar procedure to example 1 (Step 5-6), except substituting 6-chloro-2-methyl-4-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)pyridazin-3(2H)-one for 6-chloro-2-methyl-4-(5-(1-methylpiperidin-4-yl)pyridin-2-ylamino)pyridazin-3(2H)-one and substituting 2-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-4-iodo-pyridine-3-carbaldehyde for 2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-iodonicotinaldehyde in step 5 afforded 72 mg of the title compound as a white solid. (M+H)+=568 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.45 (s, 9 H) 2.54 (s, 3 H) 2.97 (br. s., 2 H) 3.68 (s, 2 H) 3.90 (s, 3 H) 4.08 (t, J=6.99 Hz, 1 H) 4.17 (t, J=5.48 Hz, 2 H) 4.47-4.56 (m, 2 H) 5.86 (s, 1 H) 7.62 (d, J=4.91 Hz, 1 H) 7.77 (d, J=1.89 Hz, 1 H) 7.86-8.01 (m, 3 H) 8.38 (s, 1 H) 8.44 (d, J=8.31 Hz, 1 H) 8.72 (d, J=4.91 Hz, 1 H).

Workup

  1. customPreparation by a similar procedure to example 1 (Step 5-6)

Sources & evidence

ORD record
ord-6bdb96eb0b6f48eaacc698c037dac72e
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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