HCID 57919133, compound → HCID 44463506, compound

HRID 2381449Notes

Reaction equation

HRID 2381449 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:13](O)=[O:14])[C:9](=[O:11])[CH:10]=1.[NH2:28][C:29]1[CH:33]=[CH:32][N:31]([CH2:34][C:35]([CH3:38])([OH:37])[CH3:36])[N:30]=1>>[F:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:2]([F:1])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:13]([NH:28][C:29]2[CH:33]=[CH:32][N:31]([CH2:34][C:35]([OH:37])([CH3:36])[CH3:38])[N:30]=2)=[O:14])[C:9](=[O:11])[CH:10]=1

Participants

3

Reactant 2

HCID 57919133HCID 57919133, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44463506HCID 44463506, compoundYield 37%

Procedure

Using the method described in Example 17, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-(tetrahydro-pyran-4-yl)-propionic acid (Intermediate 32) 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]-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-3-(tetrahydro-pyran-4-yl)-propionamide as a white solid (0.11 g, 37%); ES+-HRMS m/e calcd for C25H29N5O5F2 [M+H+] 518.2210 found 518.2210. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H) 1.07 (s, 3H) 1.12-1.62 (m, 5H) 1.81-1.96 (m, 1H) 2.13-2.28 (m, 1H) 3.08-3.28 (m, 2H) 3.70-3.86 (m, 2H) 3.90 (s, 2H) 4.67 (s, 1H) 5.55 (dd, J=11.1, 4.3 Hz, 1H) 6.04 (d, J=3.0 Hz, 1H) 6.40 (d, J=2.3 Hz, 1H) 7.34-7.43 (m, 2H) 7.43-7.52 (m, 1H) 7.53 (d, J=2.3 Hz, 1H) 8.30 (d, J=3.0 Hz, 1H) 10.86 (s, 1H).

Sources & evidence

ORD record
ord-8bddc425aa5946d9aa54d51f95f4ac5c
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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