Phosphorus oxychloride → HCID 178436101, 화합물

HRID 2169177

반응식

HRID 2169177 반응식
[CH2:1]([O:8][C:9]1[C:10]([C:29](O)=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:32]([O:39][CH2:40][CH2:41][NH:42][CH:43]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH3:44])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].O=P(Cl)(Cl)Cl.C(O)CO.C(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([C:29]([N:42]([CH2:41][CH2:40][O:39][Si:32]([C:35]([CH3:36])([CH3:38])[CH3:37])([CH3:34])[CH3:33])[CH:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH3:44])=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 24813Phosphorus oxychlorideHCID 86601574Dry ice ethyleneglycolHCID 867258282-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamineHCID 178524871HCID 178524871, 화합물

생성물 1

HCID 178436101HCID 178436101, 화합물수율 81.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

To a solution of 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxypyrimidine-4-carboxylic acid (28-02) (170 mg, 387 μmol, Eq: 1.00) and 2-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine (34) (108 mg, 387 μmol, Eq: 1.00) in pyridine (2.00 ml) was added POCl3 (178 mg, 108 μl, 1.16 mmol, Eq: 3.00) at −10° C. (ethylene glycol-dry-ice bath), then the reaction mixture was stirred at 0° C. for 2 hr. The reaction mixture was quenched with ice cooled-water (0.5 ml), concentrated, and chromatographed (silica gel, gradient 5 to 30% ethyl acetate-hexane) to obtain 5-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(1-phenylethyl)pyrimidine-4-carboxamide (35) (220 mg, 314 μmol, 81.1% yield).

후처리

  1. customThe reaction mixture was quenched with ice
  2. temperaturecooled-water (0.5 ml)
  3. concentrationconcentrated
  4. customchromatographed (silica gel, gradient 5 to 30% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-02f24d3b6f9c482f860936e7862f1ab7
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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