4-Methylmorpholine → N-(2-Amino-2-oxoethyl)-1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-N-methyl-1H-indole-6-carboxamide

HRID 630543노트

반응식

HRID 630543 반응식
CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[CH3:31][NH:32][CH2:33][C:34]([NH2:36])=[O:35].[CH2:37]([C:39]1[CH:40]=[CH:41][C:42]([F:66])=[C:43]([C:45]2[CH:46]=[N:47][C:48]([N:51]3[C:59]4[C:54](=[CH:55][CH:56]=[C:57]([C:60]([OH:62])=O)[CH:58]=4)[C:53]([CH:63]([OH:65])[CH3:64])=[CH:52]3)=[N:49][CH:50]=2)[CH:44]=1)[CH3:38]>CN(C=O)C>[NH2:36][C:34](=[O:35])[CH2:33][N:32]([CH3:31])[C:60]([C:57]1[CH:58]=[C:59]2[C:54]([C:53]([CH:63]([OH:65])[CH3:64])=[CH:52][N:51]2[C:48]2[N:47]=[CH:46][C:45]([C:43]3[CH:44]=[C:39]([CH2:37][CH3:38])[CH:40]=[CH:41][C:42]=3[F:66])=[CH:50][N:49]=2)=[CH:55][CH:56]=1)=[O:62]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 138929562-(Methylamino)acetamide hydrochlorideHCID 1186660901-(5-(5-Ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indole-6-carboxylic acid

생성물 1

HCID 118666127N-(2-Amino-2-oxoethyl)-1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-N-methyl-1H-indole-6-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-methylmorpholine (0.107 mL, 0.986 mmol), TBTU (0.191 g, 0.592 mmol) and 2-(methylamino)acetamide hydrochloride (0.123 g, 0.986 mmol) were added to an ice-cooled suspension of 331e) (0.2 g, 0.493 mmol) in DMF (4 mL). The reaction mixture was stirred at room temperature for 16 h and then diluted with ice-cold water. A precipitate was filtered off and dissolved in dichloromethane. The organic phase was washed with sodium hydrogen carbonate solution (20 mL) and brine (20 mL), dried over sodium sulfate and evaporated. The remnant was purified by flash column chromatography [silica gel; dichloromethane with 4% methanol] followed by preparative HPLC. White solid. Yield: 65 mg (28% of theory)

후처리

  1. temperaturecooled
  2. additiondiluted with ice-cold water
  3. filtrationA precipitate was filtered off
  4. dissolutiondissolved in dichloromethane
  5. washThe organic phase was washed with sodium hydrogen carbonate solution (20 mL) and brine (20 mL)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe remnant was purified by flash column chromatography [silica gel; dichloromethane with 4% methanol]

출처 및 근거

ORD 기록
ord-85b6c7498c2f4a49a6f611d1aa61adbd
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315490B2

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