HCID 117702792, compound → HCID 86292386, compound

HRID 873916Notes

Reaction equation

HRID 873916 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:30][C:31]2[CH:32]=[C:33]([CH3:41])[C:34]3[N:35]([C:37]([CH3:40])=[N:38][N:39]=3)[CH:36]=2)[C:9]2[C:10]([C:27](O)=[O:28])=[N:11][N:12]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:13]=2[CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:9]3[C:10](=[N:11][N:12]([C:17]4[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=4)[C:13]=3[CH:14]([CH3:16])[CH3:15])[C:27](=[O:28])[N:30]2[C:31]2[CH:32]=[C:33]([CH3:41])[C:34]3[N:35]([C:37]([CH3:40])=[N:38][N:39]=3)[CH:36]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 117702792HCID 117702792, compound

Product 1

HCID 86292386HCID 86292386, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Example 1 using 4-((4-chlorophenyl)((3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)amino)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylic acid (Step 67.6) in a mixture CH2Cl2/DMF 20:1 for 30 min at RT. Purification by preparative achiral SFC (diethyl-amino, gradient 11-16% in 6 min_total 11 min). tR: 1.01 min (LC-MS 2); ESI-MS: 559 [M+H]+ (LC-MS 2); Rf=0.40 (CH2Cl2/MeOH 10:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.49 (d, J=6.8 Hz, 3H) 1.16 (d, J=6.8 Hz, 3H) 2.46 (s, 3H) 2.66 (m, 4H) 3.96 (s, 3H) 4.01 (s, 3H) 6.65 (s, 1H) 7.22-7.68 (m, 5H) 8.49 (s, 1H) 8.64 (s, 1H).

Workup

  1. customPurification by preparative achiral SFC (diethyl-amino, gradient 11-16% in 6 min_total 11 min)

Sources & evidence

ORD record
ord-98ae6b4cb1b64081b88fa33d3ea4ed2c
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…