HCID 57919231, compound → HCID 86635178, compound

HRID 2381472Notes

Reaction equation

HRID 2381472 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:13](O)=[O:14])[C:9](=[O:11])[CH:10]=1.[CH3:27][C:28]1([CH3:40])[O:32][C@H:31]([CH2:33][N:34]2[CH:38]=[CH:37][C:36]([NH2:39])=[N:35]2)[CH2:30][O:29]1>>[CH3:27][C:28]1([CH3:40])[O:32][C@H:31]([CH2:33][N:34]2[CH:38]=[CH:37][C:36]([NH:39][C:13](=[O:14])[CH:12]([N:8]3[C:9](=[O:11])[CH:10]=[C:5]([O:4][C:3]4[C:2]([F:1])=[CH:25][CH:24]=[CH:23][C:22]=4[F:26])[CH:6]=[N:7]3)[CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[N:35]2)[CH2:30][O:29]1

Participants

3

Reactant 2

HCID 57919231HCID 57919231, compound2×HCID 59344941(R)-1-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine2×

Product 1

HCID 86635178HCID 86635178, compound

Procedure

Using the method described in Example 49, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-ethyl-hexanoic acid (Intermediate 31) and 1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-ylamine (Intermediate 4) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-ethyl-hexanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-amide as a viscous oil as a mixture of diastereomers. 1H NMR (300 MHz, CDCl3) δ ppm 0.79-0.93 (m, 6H), 1.12 (br s, 1H), 1.20-1.54 (m, 4H), 1.34 (s, 3H), 1.38 (s, 3H), 2.02-2.19 (m, 1H), 2.19-2.34 (m, 1H), 3.68-3.77 (m, 1H), 4.04 (dd, J=8.6, 6.5 Hz, 1H), 4.10 (d, J=5.4 Hz, 2H), 4.32-4.47 (m, 1H), 5.66 (dd, J=9.1, 6.0 Hz, 1H), 6.00 (br s, 1H), 6.68 (s, 1H), 7.01-7.14 (m, 2H), 7.28-7.37 (m, 2H), 8.01 (d, J=2.7 Hz, 1H), 8.59 (br s, 1H).

Sources & evidence

ORD record
ord-5ed1e756ae7d4c768151e2999d212c42
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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