HCID 57919217, compound → HCID 57919108, compound

HRID 2381542Notes

Reaction equation

HRID 2381542 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([O:27][C:28]([F:31])([F:30])[F:29])[CH:24]=[CH:23][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][CH2:20][CH2:19][CH2:18]2)[C:13](O)=[O:14])[C:9](=[O:11])[CH:10]=1.[NH2:32][C:33]1[CH:37]=[CH:36][N:35]([CH2:38][C:39]([CH3:42])([OH:41])[CH3:40])[N:34]=1>>[Cl:1][C:2]1[CH:26]=[C:25]([O:27][C:28]([F:29])([F:31])[F:30])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C:13]([NH:32][C:33]2[CH:37]=[CH:36][N:35]([CH2:38][C:39]([OH:41])([CH3:40])[CH3:42])[N:34]=2)=[O:14])[C:9](=[O:11])[CH:10]=1

Participants

3

Reactant 2

HCID 57919217HCID 57919217, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919108HCID 57919108, compoundYield 52%

Procedure

Using the method described in Example 49, 2-[4-(2-chloro-4-trifluoromethoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclohexyl-propionic acid (Intermediate 91) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(2-chloro-4-trifluoromethoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclohexyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as a white solid (130 mg, 52%); ES+-HRMS m/e calcd for C27H31N5O5F3Cl [M+H+] 598.2039 found 598.2038. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.84-1.26 (m, 6H), 1.05 (br. s., 6H), 1.63 (br. s., 5H), 1.74-1.91 (m, 1H), 2.07-2.23 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.48-5.60 (m, 1H), 5.91 (d, J=2.7 Hz, 1H), 6.39 (s, 1H), 7.45-7.60 (m, 2H), 7.67 (dd, J=9.1, 2.1 Hz, 1H), 7.87 (br. s., 1H), 8.22 (d, J=2.7 Hz, 1H), 10.82 (s, 1H).

Sources & evidence

ORD record
ord-463ce69369a943b2b4cd82a9f347067a
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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