2-Chlorophenol → 2-[4-(2-chloro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-propionamide
Reaction equation
N1([O:10][C:11]2[CH:12]=[N:13][N:14]([CH:18]([CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[C:19]([NH:21][C:22]3[CH:26]=[CH:25][N:24]([CH2:27][C@@H:28]4[CH2:32][O:31][C:30]([CH3:34])([CH3:33])[O:29]4)[N:23]=3)=[O:20])[C:15](=[O:17])[CH:16]=2)C2C=CC=CC=2N=N1.[Cl:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1O>>[Cl:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[O:10][C:11]1[CH:12]=[N:13][N:14]([CH:18]([CH2:35][CH:36]2[CH2:37][CH2:38][CH2:39][CH2:40]2)[C:19]([NH:21][C:22]2[CH:26]=[CH:25][N:24]([CH2:27][C@@H:28]3[CH2:32][O:31][C:30]([CH3:34])([CH3:33])[O:29]3)[N:23]=2)=[O:20])[C:15](=[O:17])[CH:16]=1Participants
Reactant 2
Product 1
Procedure
Using the method described in Example 126, Step 1, 2-[4-(benzotriazol-1-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-propionamide (Example 114, Step 1) and 2-chloro-phenol afforded 2-[4-(2-chloro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-propionamide as a white solid as a mixture of diastereomers (99.4 mg, 80%); ES+-HRMS m/e calcd for C27H32N5O5Cl [M+H+] 542.2165 found 542.2167. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.09 (br. s., 1H), 1.28 (br. s., 1H), 1.24 (s, 3H), 1.30 (d, J=1.8 Hz, 3H), 1.37-1.76 (m, 7H), 1.85-2.00 (m, 1H), 2.18-2.33 (m, 1H), 3.73 (dd, J=8.5, 5.7 Hz, 1H), 4.00 (dd, J=8.3, 6.5 Hz, 1H), 4.04-4.19 (m, 2H), 4.27-4.41 (m, 1H), 5.45 (dd, J=10.6, 4.2 Hz, 1H), 5.69 (d, J=3.0 Hz, 1H), 6.39 (d, J=2.1 Hz, 1H), 7.35-7.47 (m, 1H), 7.51 (m, 2H), 7.59 (s, 1H), 7.70 (d, J=7.8 Hz, 1H), 8.20 (d, J=3.0 Hz, 1H), 10.85 (br. s., 1H).
Sources & evidence
- ORD record
- ord-6bafd48e17644ed3bbdda8f651d72e81
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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