HCID 17823252, compound → HCID 46216159, compound

HRID 2367264Notes

Reaction equation

HRID 2367264 reaction equation
Cl.[C:2]1([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][NH:13][CH2:12]2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[N:22]=[C:21]([C:23]2[CH:31]=[C:30]3[C:26]([C:27]([NH2:32])=[N:28][NH:29]3)=[CH:25][CH:24]=2)[CH:20]=[C:19](S(C)(=O)=O)[N:18]=1>CN1C(=O)CCC1.CCN(C(C)C)C(C)C>[NH2:16][C:17]1[N:18]=[C:19]([N:13]2[CH2:14][CH2:15][CH:11]([C:9]([NH:8][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:12]2)[CH:20]=[C:21]([C:23]2[CH:31]=[C:30]3[C:26]([C:27]([NH2:32])=[N:28][NH:29]3)=[CH:25][CH:24]=2)[N:22]=1

Participants

5

Reactant 2

HCID 17823252HCID 17823252, compoundHCID 58504757HCID 58504757, compound

Product 1

HCID 46216159HCID 46216159, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of N-phenyl-3-pyrrolidinecarboxamide hydrochloride (500 mg, 2.21 mmol), 6-[2-amino-6-(methylsulfonyl)-4-pyrimidinyl]-1H-indazol-3-amine (500 mg, 1.6 mmol) in NMP (3 mL) and Hunig's base (1.5 mL) was heated at 160° C. for 1 hour under microwave conditions. The reaction mixture was concentrated and purified by SiO2 chromatography (eluent: 4.5:4.5:1 EtOAc:THF:NH4OH) to afford the title compound (50 mg) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 2.05 (m, 2H), 3.30 (m, 1H), 3.4-3.7 (m, 4H), 5.36 (s, 2H), 6.03 (s, 2H), 6.31 (s, 1H), 7.03 (m, 1H), 7.31 (m, 2H), 7.57-7.74 (m, 4H), 7.94 (s, 1H), 10.10 (s, 1H), 11.49 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by SiO2 chromatography (eluent: 4.5:4.5:1 EtOAc:THF:NH4OH)

Sources & evidence

ORD record
ord-9f4fbfc65fd444f990a245d717be2b6e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…