HCID 57919133, compound → HCID 57919279, compound

HRID 2381553Notes

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]([OH:15])=O)[C:9](=[O:11])[CH:10]=1.[NH2:28][C:29]1[CH:33]=[C:32]([CH3:34])[N:31]([CH2:35][CH:36]([O:38][C:39](=[O:41])[CH3:40])[CH3:37])[N:30]=1>>[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]([NH:28][C:29]2[CH:33]=[C:32]([CH3:34])[N:31]([CH2:35][CH:36]([O:38][C:39](=[O:41])[CH3:40])[CH3:37])[N:30]=2)=[O:15])[C:9](=[O:11])[CH:10]=1

Participants

Reactant 2

HCID 57919133HCID 57919133, compound2×

HCID 57919297HCID 57919297, compound2×

Product 1

HCID 57919279HCID 57919279, compound

Procedure

Using the method described in Example 49, 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-(tetrahydro-pyran-4-yl)-propionic acid (Intermediate 32) and acetic acid 2-(3-amino-5-methyl-pyrazol-1-yl)-1-methyl-ethyl ester (Intermediate 98) afforded acetic acid 2-{3-[2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-(tetrahydro-pyran-4-yl)-propionylamino]-5-methyl-pyrazol-1-yl}-1-methyl-ethyl ester as a mixture of diastereomers (180 mg, 39%); ES+-HRMS m/e calcd for C27H31N5O6F2 [M+H+] 560.2315 found 560.2313. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.09-1.45 (m, 4H), 1.17, 1.18 (2×d, J=6.4 Hz, 3H), 1.45-1.58 (m, 2H), 1.77-1.92 (m, 1H), 1.94, 1.95 (2×s, 3H), 2.22 (s, 3H), 3.09-3.28 (m, 2H), 3.73-3.86 (m, 2H), 3.97-4.14 (m, 2H), 5.01-5.18 (m, 1H), 5.53 (dd, J=10.7, 3.2 Hz, 1H), 6.04 (d, J=2.3 Hz, 1H), 6.21 (s, 1H), 7.33-7.43 (m, 2H), 7.44-7.54 (m, 1H), 8.29 (d, J=2.3 Hz, 1H), 10.75, 10.77 (2×s, 1H).

Sources & evidence

ORD record: ord-24917ddc71854f948dd7222ff619cf97
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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