HCID 57919097, compound → HCID 66892811, compound

HRID 2381468Notes

Reaction equation

HRID 2381468 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=O)[C:9](=[O:11])[CH:10]=1.[CH3:25][C:26]1([CH3:38])[O:30][C@H:29]([CH2:31][N:32]2[CH:36]=[CH:35][C:34]([NH2:37])=[N:33]2)[CH2:28][O:27]1>>[CH3:25][C:26]1([CH3:38])[O:30][C@H:29]([CH2:31][N:32]2[CH:36]=[CH:35][C:34]([NH:37][C:13](=[O:15])[CH:12]([N:8]3[C:9](=[O:11])[CH:10]=[C:5]([O:4][C:3]4[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:2]=4[F:1])[CH:6]=[N:7]3)[CH2:16][CH:17]([CH3:19])[CH3:18])=[N:33]2)[CH2:28][O:27]1

Participants

3

Reactant 2

HCID 57919097HCID 57919097, compound2×HCID 59344941(R)-1-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine2×

Product 1

HCID 66892811HCID 66892811, compound

Procedure

Using the method described in Example 49, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid (Intermediate 28) 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-methyl-pentanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-amide as an off-white solid as a mixture of diastereoisomers (1.21 g, 79%); ES+-HRMS m/e calcd for C25H29N5O5F2 [M+H+] 518.2210 found 518.2214. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.87 (d, J=6.6 Hz, 3H), 0.89 (d, J=6.6 Hz, 3H), 1.25 (s, 3H), 1.30, 1.31 (2×s, 3H), 1.38-1.51 (m, 1H), 1.74-1.85 (m, 1H), 2.12-2.24 (m, 1H), 3.74 (dd, J=8.4, 5.9 Hz, 1H), 3.97-4.17 (m, 3H), 4.35 (m, 1H), 5.52 (dd, J=11.2, 4.2 Hz, 1H), 6.04 (d, J=2.7 Hz, 1H), 6.39 (d, J=2.1 Hz, 1H), 7.35-7.43 (m, 2H), 7.43-7.55 (m, 1H), 7.60 (m, 1H), 8.28 (d, J=2.7 Hz, 1H), 10.85 (s, 1H).

Sources & evidence

ORD record
ord-b3185bf63f73408dbc5377c86fdb014e
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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