4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 68557157, compound

HRID 2382050Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([OH:16])=O)=[CH:9][N:8]=1.[CH3:17][O:18][C:19]([C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:30])[CH:28]=2)[N:23]([NH2:31])[CH:22]=1)=[O:20].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH3:17][O:18][C:19]([C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:30])[CH:28]=2)[N:23]([NH:31][C:14]([C:10]2[C:11]([CH3:13])=[N:12][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:8][CH:9]=2)=[O:16])[CH:22]=1)=[O:20]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 2-(2-pyridyl)-4-methyl-pyrimidine-5-carboxylic acid (559 mg, 2.6 mmol) and 1-amino-5-fluoro-1H-indole-3-carboxylic acid methyl ester (540 mg, 2.6 mmol) in DMF (25 mL) is stirred at 50° C. for 0.5 h. The mixture is treated with DMTMM (718 mg, 2.6 mmol) and stirred at 50° C. for 1 h. The mixture is diluted with saturated aqueous Na2CO3 (50 mL), and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 1%-10% MeOH in DCM to afford 5-fluoro-1-[(4-methyl-2-pyridin-2-yl-pyrimidine-5-carbonyl)-amino]-1H-indole-3-carboxylic acid methyl ester.

Workup

extractionextracted with EtOAc (3×50 mL)
dry with materialThe combined organic layer is dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is purified by silica gel chromatography
washeluting with 1%-10% MeOH in DCM

Sources & evidence

ORD record: ord-ef8498a4adae4157b50bdc67f939415d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

Loading…