Methylamine → HCID 86700186, compound

HRID 879376Notes

Reaction equation

HRID 879376 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:44]([CH3:45])=[CH:43][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:32](=[CH:33][CH:34]=4)[N:31]=[C:30](OS(C(F)(F)F)(=O)=O)[CH:29]=[CH:28]5)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:46]1[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:53][NH2:54]>C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:44]([CH3:45])=[CH:43][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]4[CH:26]=[C:27]5[C:32](=[CH:33][CH:34]=4)[N:31]=[C:30]([NH:54][CH3:53])[CH:29]=[CH:28]5)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:46]1[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86700185HCID 86700185, compound

Product 1

HCID 86700186HCID 86700186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-(trifluoromethylsulfonyloxy)quinolin-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (28.0 mg, 0.036 mmol) and 1.0 mL of methylamine at 2M in THF were heating at 80° C. for 3 days. Concentrated in vacuo and then purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C37H36ClN4O3S: 651.2; found: 651.3.

Workup

  1. concentrationConcentrated in vacuo
  2. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8e98278a011547af8d851f490548d5cc
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…