Diisopropylethylamine → HCID 178489797, 화합물

HRID 1911405

반응식

HRID 1911405 반응식
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[NH:12][N:13]=[C:14]([CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=3)[CH:15]=2)=[O:9])=[N:6][CH:7]=1.CN1[C@@H](C)CNC[C@H]1C.[CH3:37][C@H:38]1[CH2:43][NH:42][CH2:41][C@@H:40]([CH3:44])[N:39]1[CH2:45][C:46]#[N:47].C(N(C(C)C)C(C)C)C>CS(C)=O.CO>[C:46]([CH2:45][N:39]1[C@@H:38]([CH3:37])[CH2:43][N:42]([C:2]2[N:3]=[CH:4][C:5]([C:8]([NH:10][C:11]3[NH:12][N:13]=[C:14]([CH2:16][CH2:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=4)[CH:15]=3)=[O:9])=[N:6][CH:7]=2)[CH2:41][C@H:40]1[CH3:44])#[N:47]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 30720221(2R,6S)-1,2,6-TrimethylpiperazineHCID 866210742-[(2S,6R)-2,6-dimethylpiperazin-1-yl]acetonitrileHCID 178489782HCID 178489782, 화합물

생성물 1

HCID 178489797HCID 178489797, 화합물수율 22%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매

실험 절차

5-Chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (271 mg, 0.70 mmol) was added in one portion to a 3:1 mixture of (2R,6S)-1,2,6-trimethylpiperazine and 2-[(2S,6R)-2,6-dimethylpiperazin-1-yl]acetonitrile (180 mg, 1.40 mmol) in anhydrous dimethylsulfoxide (1.40 ml) at 25° C. The resulting solution was stirred at ambient temperature for 2 h. The reaction was incomplete and N-ethyl-N-propan-2-ylpropan-2-amine (0.24 ml, 1.40 mmol) was added and the solution was stirred at 60° C. for a further 2 h. The reaction mixture was diluted with methanol (20 mL) and purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH to afford impure material. The concentrated eluent was purified by silica column chromatography, eluting with a gradient of 0 to 5% 7M NH3/MeOH in DCM. Pure fractions were evaporated to dryness to afford the title compound (77 mg, 22%) as a yellow solid.

후처리

  1. stirringthe solution was stirred at 60° C. for a further 2 h
  2. custompurified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customto afford impure material
  5. customThe concentrated eluent was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 5% 7M NH3/MeOH in DCM
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-7d7f20f4ffa9475a8273d114cc74ffdd
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604022B2

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