Cesium carbonate → N-(2-(2,6-Dichlorophenyl)thiazolo[5,4-c]pyridin-4-yl)-2-(dimethylamino)acetamide

HRID 2366185ノート

反応式

HRID 2366185 の反応式
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH3:19][N:20]([CH3:25])[CH2:21][C:22]([NH2:24])=[O:23].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([NH:24][C:22](=[O:23])[CH2:21][N:20]([CH3:25])[CH3:19])=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 2301162-(Dimethylamino)acetamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 862804124-Bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine

生成物 1

HCID 56953391N-(2-(2,6-Dichlorophenyl)thiazolo[5,4-c]pyridin-4-yl)-2-(dimethylamino)acetamide収率 25%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (60 mg, 0.17 mmol), 2-(dimethylamino)acetamide (0.023 g, 0.22 mmol), Pd2(dba)3 (0.013 g, 0.017 mmol), XantPhos (0.017 g, 0.034 mmol) and Cs2CO3 (0.11 g, 0.34 mmol) in dioxane (3.0 mL). The mixture was degassed with N2 for 10 minutes and then irradiated in a microwave reactor at 160° C. for 2 hours. After cooling to room temperature the solid was removed via filtration. The filtrate was concentrated under reduced pressure and the residue was purified by reverse phase column chromatography, eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a white solid (15 mg, 25% yield). 1H NMR (500 MHz, DMSO-d6): δ 10.62 (s, 1H), 8.46 (d, J=6.0 Hz, 1H), 7.96 (d, J=6.0 Hz, 1H), 7.74-7.65 (m, 3H), 3.24 (s, 2H), 2.49 (s, 6H). LCMS (Method B): RT=6.01 min, m/z: 381.1 [M+H+].

後処理

  1. customThe mixture was degassed with N2 for 10 minutes
  2. customirradiated in a microwave reactor at 160° C. for 2 hours
  3. customwas removed via filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by reverse phase column chromatography
  6. washeluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3

出典と根拠

ORDレコード
ord-18fb0ffe89604d1e94a2a5a822e85c14
出典データセット
uspto-grants-2014_04
特許番号
US08697708B2

反応ノート

読み込み中…