Valeryl chloride → HCID 19783157, 화합물

HRID 257559노트

반응식

HRID 257559 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:48])=[C:6]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[S:31](=[O:43])(=[O:42])[NH:32][C:33](=[O:41])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[Cl:40])=[CH:21][CH:20]=3)[C:10]([CH2:44][CH2:45][CH2:46][CH3:47])=[N:9]2)[CH:7]=1.[C:49](Cl)(=[O:54])[CH2:50][CH2:51][CH2:52][CH3:53]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH2:44]([C:10]1[C:11]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[S:31](=[O:42])(=[O:43])[NH:32][C:33](=[O:41])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])=[CH:23][CH:24]=2)=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:49](=[O:54])[CH2:50][CH2:51][CH2:52][CH3:53])[CH:3]=[CH:4][C:5]=2[Cl:48])[N:9]=1)[CH2:45][CH2:46][CH3:47]

참가 물질

5

반응물 2

HCID 61186Valeryl chlorideHCID 19783146HCID 19783146, 화합물

생성물 1

HCID 19783157HCID 19783157, 화합물수율 73.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

To a mixture of 150 mg (0.213 mmol) of ethyl 1-(5-amino-2-chlorophenyl)-3-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-biphenyl-4-yl]methyl]-1H-pyrazole-5-carboxylate (from Step I), 26 mg (0.213 mmol) of 4-(dimethylamino)pyridine (DMAP), and 1.75 mL of dry pyridine was added 126 μL (128 mg, 1.06 mmol) of valeryl chloride. The mixture was stirred under N2 at room temperature overnight and then partitioned between H2O and ethyl acetate. The organic layer was washed twice with H2O and then with brine. Next, the ethyl acetate phase was dried over Na2SO4, filtered, and rotary-evaporated in vacuo. The yellow-orange residual oil was flash chromatographed on silica gel (gradient elution with 0.5-3% MeOH in CH2Cl2) to give 123 mg (72%) of the title compound as a slightly yellow solid, mp>95° C. (gradual); homogeneous by TLC in 95:5 CH2Cl2 -- MeOH; mass spectrum (FAB) m/e 827 (M+K)+. 400 MHz 1H NMR (CDCl3) δ0.87 (t, J=7.3 Hz, 3H), 0.92 (t, J=7.4 Hz, 3H), 1.02 (t, J=7.1 Hz, 3H), 1.29-1.40 (m, 4H), 1.57 (m, 2H), 1.67 (m, 2H), 2.32 (t, J=7.6 Hz, 2H), 2.53 (t, J=7.8 Hz, 2H), 4.05-4.15 (m, 4H), 7.06 (d, J=8.2 Hz, 2H), 7.21-7.66 (m, 10H), 7.75 (d, J=2.4 Hz, 1H), 8.27 (s, 1H), 8.34 (dd, J=8.0, 1.3 Hz, 1H).

후처리

  1. custompartitioned between H2O and ethyl acetate
  2. washThe organic layer was washed twice with H2O
  3. dry with materialNext, the ethyl acetate phase was dried over Na2SO4
  4. filtrationfiltered
  5. customrotary-evaporated in vacuo
  6. customchromatographed on silica gel (gradient elution with 0.5-3% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-f5f7edc12d1a4f9d95d3aa38c0bcfecb
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262412

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