4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one → HCID 57919263, compound

HRID 2381383Notes

Reaction equation

HRID 2381383 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][C:17]1[N:22]=[C:21]([OH:23])[CH:20]=[CH:19][CH:18]=1.C[O:25][C:26](=[O:35])[CH:27](Br)[CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([CH2:28][CH:27]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:23][C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:16])[N:22]=3)[CH:6]=[N:5]2)[C:26]([OH:25])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 3

HCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×HCID 178425782HCID 178425782, compound

Product 1

HCID 57919263HCID 57919263, compound

Procedure

In an analogous manner to the stepwise sequence outlined in intermediate 19, starting from 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 6-methyl-pyridin-2-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(6-methyl-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (9.7 g, 66% for the final step); LC-MS: tR=3.28 min, 344 [M+H]+. HPLC: tR=9.16 min, 95.62% at 214 nm, 96.87% at 254 nm. 1H NMR (300 MHz, DMSO-d6): δ13.04 (broad, 1H), 8.07 (d, 1H, J=2.4 Hz), 7.89 (t, 1H, J=7.5 Hz), 7.21 (d, 1H, J=7.2 Hz), 7.06 (d, 1H, J=8.4 Hz), 6.52 (d, 1H, J=2.4 Hz), 5.36 (dd, 1H, J=10.5 Hz, J=4.2 Hz), 2.43 (s, 3H), 2.23-2.17 (m, 1H), 2.02-2.00 (m, 1H), 1.70-1.44 (m, 7H), 1.13-1.05 (m, 2H).

Sources & evidence

ORD record
ord-f6913c7a07a741abaec969ba42e5865b
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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