1,2-Dichloroethane → HCID 178494981, 화합물

HRID 1254381노트

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HRID 1254381 반응식
[C:1]([NH:3][C:4]([NH:6][C@@H:7]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:8][N:9]([CH3:19])[C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])=S)#[N:2].Cl[C:28]1[CH:29]=[C:30]([C@:34]([C@@H:42]2[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]2)([OH:41])[CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:31]=[CH:32][CH:33]=1.C(Cl)CCl>CN(C=O)C.CCOCC>[C:1]([N:3]=[C:4]([N:44]1[CH2:45][CH2:46][CH2:47][C@@H:42]([C@:34]([OH:41])([C:30]2[CH:29]=[CH:28][CH:33]=[CH:32][CH:31]=2)[CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH2:43]1)[NH:6][C@@H:7]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:8][N:9]([CH3:19])[C:10]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])#[N:2]

참가 물질

6

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HCID 111,2-DichloroethaneHCID 59382814(S)-1-(3-chlorophenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-olHCID 866530841-cyano-3-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)thiourea

생성물 1

HCID 178494981HCID 178494981, 화합물수율 38.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 1-cyano-3-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)thiourea (230 mg, 0.58 mmol) and (S)-1-(3-chlorophenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (180 mg, 0.58 mmol) in DMF (5 mL) was added EDC (0.17 g, 0.87 mmol). The mixture was stirred for 16 h at rt, diluted with ether (175 mL) and washed with 5% aq HCl (2×50 mL) and brine (50 mL). The combined aqueous washes were back extracted with ether. The combined ether extracts were concentrated to afford crude product (290 mg). The mixture was purified by prep HPLC to afford (3R)—N′-cyano-N-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carboxamidine (145 mg, 37%).

후처리

  1. washwashed with 5% aq HCl (2×50 mL) and brine (50 mL)
  2. extractionThe combined aqueous washes were back extracted with ether
  3. concentrationThe combined ether extracts were concentrated
  4. customto afford crude product (290 mg)
  5. customThe mixture was purified by prep HPLC

출처 및 근거

ORD 기록
ord-750818732a834778b01446eae5573fb0
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455521B2

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