4-Methyl-2-Pentanol → 4-[(2-cyclopentyl-4,4-diethyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide

HRID 2234318

반응식

HRID 2234318 반응식
Cl[C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:23])[C:7](=[O:22])[C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:36][C:37]1[CH:55]=[CH:54][C:40]([C:41]([NH:43][CH2:44][C:45]([CH3:53])([CH3:52])[CH2:46][N:47]2[CH2:51][CH2:50][CH2:49][CH2:48]2)=[O:42])=[CH:39][C:38]=1[O:56][CH3:57].CC(C)CC(O)C>CO>[CH:13]1([N:10]2[CH2:9][C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:7](=[O:22])[N:6]([CH3:23])[C:5]3[C:11]2=[N:12][C:2]([NH:36][C:37]2[CH:55]=[CH:54][C:40]([C:41]([NH:43][CH2:44][C:45]([CH3:52])([CH3:53])[CH2:46][N:47]4[CH2:51][CH2:50][CH2:49][CH2:48]4)=[O:42])=[CH:39][C:38]=2[O:56][CH3:57])=[N:3][CH:4]=3)[CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

6

반응물 4

HCID 79104-Methyl-2-PentanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 686858814-amino-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide2회HCID 8661756310-Chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one2회

생성물 1

HCID 686849234-[(2-cyclopentyl-4,4-diethyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide수율 27.5%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
120 °C

실험 절차

10-chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 250; 111 mg, 0.33 mmol), p-toluenesulphonic acid monohydrate (155 mg, 0.81 mmol) and 4-amino-N-(2,2-dimethyl-3-pyrrolidin-1-yl-propyl)-3-methoxy-benzamide (Intermediate 206; 100 mg, 0.33 mmol) were added to 4-methyl-2-pentanol (7 mL). The reaction was heated at 120° C. over the weekend. The sample was transferred to an SCX cartridge (10 g) pre-wet with methanol, then washed with methanol and eluted with methanolic ammonia. Product containing fractions were combined and evaporated and the resultant material purified by base modified reverse phase preparative HPLC to yield the title compound as a white solid (55 mg, 27%).

후처리

  1. washwashed with methanol
  2. washeluted with methanolic ammonia
  3. additionProduct containing fractions
  4. customevaporated
  5. customthe resultant material purified by base modified reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-60b4843b9356418ca573b23f27335ab6
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709471B2

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