3-cyclohexyl-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid → 3-cyclohexyl-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-6-oxo-6H-pyridazin-1-yl]-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide

HRID 2381555Notes

Reaction equation

HRID 2381555 reaction equation
[CH:1]1([CH2:7][CH:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([O:19][C:20]3[C:29]4[O:28][CH2:27][CH2:26][O:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH:14]=[N:13]2)[C:9](O)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:30][C:31]1[CH:35]=[CH:34][N:33]([CH2:36][C:37]([CH3:40])([OH:39])[CH3:38])[N:32]=1>>[CH:1]1([CH2:7][CH:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([O:19][C:20]3[C:29]4[O:28][CH2:27][CH2:26][O:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH:14]=[N:13]2)[C:9]([NH:30][C:31]2[CH:35]=[CH:34][N:33]([CH2:36][C:37]([OH:39])([CH3:40])[CH3:38])[N:32]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 579192533-cyclohexyl-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 444669303-cyclohexyl-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-6-oxo-6H-pyridazin-1-yl]-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamideYield 22%

Procedure

Using the method described in Example 49, 3-cyclohexyl-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 99) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 3-cyclohexyl-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-6-oxo-6H-pyridazin-1-yl]-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as an off-white solid (40 mg, 22%); ES+-HRMS m/e calcd for C28H35N5O6 [M+H+] 538.2660 found 538.2660. 1H NMR (300 MHz, CDCl3) δ ppm 0.73-1.34 (m, 6H), 1.16 (br. s., 3H), 1.16 (br. s., 3H), 1.54-1.85 (m, 5H), 1.96-2.29 (m, 2H), 3.99 (s, 2H), 4.20-4.37 (m, 4H), 5.59-5.79 (m, 1H), 6.00 (d, J=2.7 Hz, 1H), 6.64-6.77 (m, 2H), 6.78-6.95 (m, 2H), 7.32 (s, 1H), 7.96 (d, J=2.7 Hz, 1H), 8.77 (br. s., 1H).

Sources & evidence

ORD record
ord-7ee644d7e3e4492d8045b07c74e3f6ec
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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