Diisopropylethylamine → (R)-1-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarbonyl)-piperidine-3-carboxylic acid ethyl ester

HRID 237434

반응식

HRID 237434 반응식
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]2[CH2:30][CH2:29][CH:28]([C:31]([O-])=[O:32])[CH2:27][CH2:26]2)[N:19]=1)(=[O:4])=[O:3].[Na+].[CH2:35]([O:37][C:38]([C@@H:40]1[CH2:45][CH2:44][CH2:43][NH:42][CH2:41]1)=[O:39])[CH3:36].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>O.CN(C=O)C>[CH2:35]([O:37][C:38]([C@@H:40]1[CH2:45][CH2:44][CH2:43][N:42]([C:31]([CH:28]2[CH2:27][CH2:26][CH:25]([NH:24][C:20]3[N:19]=[C:18]([N:13]4[C:14]5[C:10](=[C:9]([O:8][CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH:17]=[CH:16][CH:15]=5)[CH:11]=[CH:12]4)[CH:23]=[CH:22][N:21]=3)[CH2:30][CH2:29]2)=[O:32])[CH2:41]1)=[O:39])[CH3:36]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 86659980Sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylate

생성물 1

HCID 54754660(R)-1-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarbonyl)-piperidine-3-carboxylic acid ethyl ester수율 8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylate (0.4 g), (R)-piperidine-3-carboxylic acid ethyl ester (0.165 g), BOP (0.537 g) and DIPEA (0.56 mL) were added to DMF (3 mL), and the mixture was stirred at room temperature overnight. The mixture was diluted with water and the resulting precipitate was collected by filtration, washed with water, dried under reduced pressure, and purified by flash chromatography (DCM/MeOH) to give 39.6 mg of (R)-1-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarbonyl)-piperidine-3-carboxylic acid ethyl ester, MP=175.0-177.0° C.

후처리

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure
  4. custompurified by flash chromatography (DCM/MeOH)

출처 및 근거

ORD 기록
ord-e0ad66e339c2487e8f8fad8c61234c2f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642601B2

연결된 노트

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