HCID 57919231, compound → HCID 44464795, compound

HRID 2381458Notes

Reaction equation

HRID 2381458 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]([OH:15])=O)[C:9](=[O:11])[CH:10]=1.[NH2:27][C:28]1[CH:32]=[CH:31][N:30]([CH2:33][C:34]([CH3:37])([OH:36])[CH3:35])[N:29]=1>>[OH:36][C:34]([CH3:37])([CH3:35])[CH2:33][N:30]1[CH:31]=[CH:32][C:28]([NH:27][C:13](=[O:15])[CH:12]([N:8]2[C:9](=[O:11])[CH:10]=[C:5]([O:4][C:3]3[C:22]([F:26])=[CH:23][CH:24]=[CH:25][C:2]=3[F:1])[CH:6]=[N:7]2)[CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[N:29]1

Participants

3

Reactant 2

HCID 57919231HCID 57919231, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44464795HCID 44464795, compoundYield 31%

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-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-ethyl-hexanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide as an off-white solid (50 mg, 31%); ES+-HRMS m/e calcd for C25H31N5O4F2 [M+H+] 504.2417 found 504.2417. 1H-NMR (400 MHz, CDCl3-d) δ ppm 0.86 (t, J=7.5 Hz, 3H) 0.87 (t, J=7.5 Hz, 3H) 1.08-1.14 (m, 1H) 1.15 (s, 3H) 1.16 (s, 3H) 1.21-1.50 (m, 4H) 2.01-2.19 (m, 1H) 2.19-2.37 (m, 1H) 3.93 (s, 2H) 5.67 (dd, J=9.6, 5.8 Hz, 1H) 6.01 (d, J=3.0 Hz, 1H) 6.72 (d, J=2.3 Hz, 1H) 7.08 (t, J=8.0 Hz, 2H) 7.27-7.33 (m, 2H) 8.01 (d, J=3.0 Hz, 1H) 8.59 (s, 1H).

Sources & evidence

ORD record
ord-1b200137c2e141958754ebec5d5ea668
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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