N-methyl-2-pyrrolidone → HCID 117601785, compound

HRID 1773707Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:17])[C:10]([NH:14][CH2:15][CH3:16])=[C:11](I)[CH:12]=2)=[C:5]([CH3:18])[O:4][N:3]=1.[CH3:19][C:20]1[C:21](B(O)O)=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][CH:24]=[CH:23]2.N12CCCN=C1CCCCC2.CN1CCCC1=O>CCOC(C)=O.[Cl-].[NH4+].O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:17])[C:10]([NH:14][CH2:15][CH3:16])=[C:11]([C:21]3[C:20]([CH3:19])=[CH:29][CH:28]=[C:27]4[C:22]=3[CH:23]=[CH:24][CH:25]=[N:26]4)[CH:12]=2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

4-(3,5-Dimethylisoxazol-4-yl)-N1-ethyl-6-iodobenzene-1,2-diamine (105 mg, 0.29 mmol), 6-methylquinolin-5-ylboronic acid (274.86 mg, 1.47 mmol), 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.26 mL, 1.76 mmol), 1-Methyl-2-pyrrolidinone (5 mL), and water (2 mL) were placed in microwave vial, pre-stirred for 2 minutes, then heated to 110° C. for 15 minutes. Reaction mixture was diluted with EtOAc and aqueous ammonium chloride and extracted with EtOAc (3 times). Organics were washed with ammonium chloride, water and brine and dried over sodium sulfate. Solvent was evaporated to dryness. Crude material was purified by silica gel chromatography (DCM/MeOH as eluent) to afford 4-(3,5-dimethylisoxazol-4-yl)-N1-ethyl-6-(6-methylquinolin-5-yl)benzene-1,2-diamine.

Workup

customReaction mixture
extractionextracted with EtOAc (3 times)
washOrganics were washed with ammonium chloride, water and brine
dry with materialdried over sodium sulfate
customSolvent was evaporated to dryness
customCrude material was purified by silica gel chromatography (DCM/MeOH as eluent)

Sources & evidence

ORD record: ord-ff08b13ddac44a36925b41bb846ddb2e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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