HCID 57919282, compound → HCID 66894174, compound

HRID 2381462Notes

Reaction equation

HRID 2381462 reaction equation
[CH:1]1([CH2:5][CH:6]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([O:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=3[F:25])[CH:12]=[N:11]2)[C:7](O)=[O:8])[CH2:4][CH2:3][CH2:2]1.[C:26]([Si:30]([CH3:41])([CH3:40])[O:31][CH2:32][CH2:33][N:34]1[CH:38]=[CH:37][C:36]([NH2:39])=[N:35]1)([CH3:29])([CH3:28])[CH3:27]>>[C:26]([Si:30]([CH3:41])([CH3:40])[O:31][CH2:32][CH2:33][N:34]1[CH:38]=[CH:37][C:36]([NH:39][C:7](=[O:8])[CH:6]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([O:17][C:18]3[C:19]([F:25])=[CH:20][CH:21]=[CH:22][C:23]=3[F:24])[CH:12]=[N:11]2)[CH2:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[N:35]1)([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 57919282HCID 57919282, compound2×HCID 593449471-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine2×

Product 1

HCID 66894174HCID 66894174, compoundYield 40%

Procedure

Using the method described in Example 49, 3-cyclobutyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 29) and 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine (Intermediate 3) afforded N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-yl}-3-cyclobutyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionamide as an off-white solid (342.2 mg, 40%); ES+-HRMS m/e calcd for C28H37N5O4SiF2 [M+H+] 574.2656 found 574.2656. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.07 (s, 6H) 0.80 (s, 9H) 1.49-1.67 (m, 1H) 1.68-2.02 (m, 5H) 2.03-2.30 (m, 3H) 3.86 (t, J=5.2 Hz, 2H) 4.06 (t, J=5.2 Hz, 2H) 5.28-5.38 (m, 1H) 6.01 (d, J=2.7 Hz, 1H) 6.36 (d, J=2.1 Hz, 1H) 7.33-7.43 (m, 2H) 7.43-7.51 (m, 1H) 7.53 (d, J=2.1 Hz, 1H) 8.26 (d, J=2.7 Hz, 1H) 10.78 (s, 1H).

Sources & evidence

ORD record
ord-f93cfa8ccd404c999d03a53c788453e9
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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