HCID 57919231, compound → HCID 86635177, compound

HRID 2381461Notes

Reaction equation

HRID 2381461 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.[C:27]([Si:31]([CH3:42])([CH3:41])[O:32][CH2:33][CH2:34][N:35]1[CH:39]=[CH:38][C:37]([NH2:40])=[N:36]1)([CH3:30])([CH3:29])[CH3:28]>>[C:27]([Si:31]([CH3:42])([CH3:41])[O:32][CH2:33][CH2:34][N:35]1[CH:39]=[CH:38][C:37]([NH:40][C:13](=[O:15])[CH:12]([N:8]2[C:9](=[O:11])[CH:10]=[C:5]([O:4][C:3]3[C:2]([F:1])=[CH:25][CH:24]=[CH:23][C:22]=3[F:26])[CH:6]=[N:7]2)[CH2:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[N:36]1)([CH3:30])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 57919231HCID 57919231, compound2×HCID 593449471-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine2×

Product 1

HCID 86635177HCID 86635177, compoundYield 49%

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-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine (Intermediate 3) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-4-ethyl-hexanoic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-amide as light yellow solid (472.6 mg, 49%). 1H NMR (300 MHz, DMSO-d6) δ ppm −0.07 (s, 6H), 0.71-0.88 (m, 6H), 0.80 (s, 9H), 0.92-1.51 (m, 5H), 1.74-1.99 (m, 1H), 2.03-2.23 (m, 1H), 3.85 (t, J=5.1 Hz, 2H), 4.06 (t, J=5.1 Hz, 2H), 5.52 (dd, J=10.7, 4.4 Hz, 1H), 6.03 (d, J=2.7 Hz, 1H), 6.36 (d, J=2.1 Hz, 1H), 7.31-7.51 (m, 3H), 7.53 (d, J=2.1 Hz, 1H), 8.28 (d, J=2.7 Hz, 1H), 10.82 (s, 1H).

Sources & evidence

ORD record
ord-602944a38fea48c282a9c70e36b622c3
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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