3(2H)-Pyridazinone → HCID 178426327, compound

HRID 2103702Notes

Reaction equation

Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:17]C[CH2:15][C@H:14]4[CH3:18])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.[CH3:21][C:22]1[C:23](=[O:28])[NH:24][CH:25]=[CH:26][CH:27]=1.N1NC(=O)C=CC=1>>[CH:14]([N:13]([CH3:17])[C@H:11]1[CH2:12][C@H:9]([C:7]2[S:8][C:4]3[CH:3]=[C:2]([N:24]4[CH:25]=[CH:26][CH:27]=[C:22]([CH3:21])[C:23]4=[O:28])[CH:20]=[CH:19][C:5]=3[N:6]=2)[CH2:10]1)([CH3:15])[CH3:18]

Participants

Reactant 3

HCID 681533(2H)-Pyridazinone

HCID 704812-Hydroxy-3-methylpyridine

HCID 178461421HCID 178461421, compound

Product 1

HCID 178426327HCID 178426327, compound

Procedure

The title compound was prepared according to the procedure described in Example 22, except for substituting the product of Example 52A for the product of Example 1E and substituting 3-methyl-2-pyridone for 3(2H)-pyridazinone. 1H NMR (400 MHz, CDCl3) δ ppm 8.02 (d, J=8.59 Hz, 1H) 7.89 (d, J=1.84 Hz, 1H) 7.42 (dd, J=8.75, 1.99 Hz, 1H) 7.23-7.34 (m, 2H) 6.18 (t, J=6.75 Hz, 1H) 3.52-3.63 (m, 1H) 3.12-3.27 (m, 1H) 2.90-3.03 (m, 1H) 2.55-2.73 (m, 2H) 2.25-2.44 (m, 2H) 2.20 (s, 3H) 2.13 (s, 3H) 1.02 (d, J=6.44 Hz, 6H). MS: (M+H)+=368.

Sources & evidence

ORD record: ord-7b8dd2c1a5f54ebf8d9788e7b6a3c491
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576110B2

Reaction notes

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