Vinyl ether → HCID 86663986、化合物

HRID 712273ノート

反応式

HRID 712273 の反応式
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:16])[NH:13][CH2:14][CH3:15])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:40]([O:42][CH2:43][CH3:44])=[CH2:41])CCC.C(OC=C)=C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:43]([O:42][C:40]([C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:16])[NH:13][CH2:14][CH3:15])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:22]=[N:21][C:20]([N:23]3[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)=[N:19][CH:18]=2)[CH:3]=1)=[CH2:41])[CH3:44]

参加物

6

反応物 3

HCID 8024Vinyl etherHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86663956Ethyl 1-(5-(7-bromo-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

生成物 1

HCID 86663986HCID 86663986、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

The ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (1 g, 1.82 mmol) and tributyl-(1-ethoxy-vinyl)-stannane (1.31 g, 3.64 mmol) were dissolved in DMF (20 mL) and the mixture deoxygenated by bubbling N2 through the solution for 20 min. Pd(PPh3)4, (210 mg, 0.18 mmol) was added and the reaction heated to 100° C. for 4 h under a N2 atmosphere, at the end of which time LCMS indicated clean formation of the vinyl ether. The reaction was concentrated under reduced pressure then diluted with EtOAc, washed with water then brine, the organic layer dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound.

後処理

  1. customthe mixture deoxygenated
  2. customby bubbling N2 through the solution for 20 min
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additionthen diluted with EtOAc
  5. washwashed with water
  6. dry with materialbrine, the organic layer dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-56b9117f236d41d0bb4de410872cb68e
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

読み込み中…