1,3-Dichloroacetone → HCID 86624337, 화합물

HRID 2362826노트

반응식

HRID 2362826 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1)#[N:2].Cl[CH2:14][C:15]([CH2:17]Cl)=O.[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[CH:30][CH:29]=2)[C:23]([C:40]#[N:41])=[C:22]([SH:42])[N:21]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[CH:32][CH:33]=2)[C:23]([C:40]#[N:41])=[C:22]([S:42][CH2:17][C:15]2[N:12]=[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[S:11][CH:14]=2)[N:21]=1

참가 물질

6

반응물 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 2757973(4-Cyanophenyl)thioureaHCID 178483863HCID 178483863, 화합물

생성물 1

HCID 86624337HCID 86624337, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 26.6 mg (0.15 mmol) of N-(4-cyanophenyl)thiourea and 19 mg (0.15 mmol) of 1,3-dichloroacetone in 0.4 ml of DMF is stirred at +80° C. for 3 h. After cooling to RT, a solution of 50.9 mg (0.15 mmol) of the compound from Example 34A in 0.2 ml of DMF and 50 mg (0.6 mmol) of sodium bicarbonate are added. The mixture is then stirred at RT for 12 h. The reaction mixture is filtered and purified directly by preparative HPLC (column: Macherey Nagel VP50/21 Nucleosil 100-5 C18 Nautilus, 5 μm, 21 mm×50 mm; wavelength: 220 nm; flow rate: 25 ml/min; mobile phase A=water+0.1% formic acid, mobile phase B=acetonitrile; gradient: 0 min 10% B→2 min 10% B→6 min 90% B→7 min 90% B→7.1 min 10% B→8 min 10% B). The product-containing fractions are combined and concentrated using a rotary evaporator.

후처리

  1. filtrationThe reaction mixture is filtered
  2. custompurified directly by preparative HPLC (column: Macherey Nagel VP50/21 Nucleosil 100-5 C18 Nautilus, 5 μm, 21 mm×50 mm; wavelength: 220 nm; flow rate: 25 ml/min; mobile phase A=water+0.1% formic acid, mobile phase B=acetonitrile; gradient: 0 min 10% B→2 min 10% B→6 min 90% B→7 min 90% B→7.1 min 10% B→8 min 10% B)
  3. concentrationconcentrated
  4. customa rotary evaporator

출처 및 근거

ORD 기록
ord-11ea1f95a082427d8b7a97265932a502
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691850B2

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