Butyl chloroformate → 4-[[2'-[N-(n-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3-n-butyl-1-[2-chloro-5-(propionylamino)phenyl]-1H-pyrazole-5-carbonitrile

HRID 257572

反応式

HRID 257572 の反応式
[CH2:1]([C:5]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23](=[O:26])(=[O:25])[NH2:24])=[CH:13][C:12]=2[F:27])=[C:8]([C:28]#[N:29])[N:7]([C:30]2[CH:35]=[C:34]([NH:36][C:37](=[O:40])[CH2:38][CH3:39])[CH:33]=[CH:32][C:31]=2[Cl:41])[N:6]=1)[CH2:2][CH2:3][CH3:4].Cl[C:43]([O:45][CH2:46][CH2:47][CH2:48][CH3:49])=[O:44].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[CH2:46]([O:45][C:43]([NH:24][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[CH:15]=[CH:16][C:11]([CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][N:7]([C:30]3[CH:35]=[C:34]([NH:36][C:37](=[O:40])[CH2:38][CH3:39])[CH:33]=[CH:32][C:31]=3[Cl:41])[C:8]=2[C:28]#[N:29])=[C:12]([F:27])[CH:13]=1)(=[O:26])=[O:25])=[O:44])[CH2:47][CH2:48][CH3:49]

参加物

4

反応物 3

HCID 61140Butyl chloroformateHCID 90495Di-tert-butyl dicarbonateHCID 197832113-n-Butyl-1-[2-chloro-5-(propionylamino)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile

生成物 1

HCID 197831764-[[2'-[N-(n-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3-n-butyl-1-[2-chloro-5-(propionylamino)phenyl]-1H-pyrazole-5-carbonitrile収率 30%

実験手順

This material was prepared by reaction of 3-n-butyl-1-[2-chloro-5-(propionylamino)phenyl]-4-[(3-fluoro-2'-sulfamoylbiphenyl-4-yl)methyl]-1H-pyrazole-5-carbonitrile (from Example 4, Step K) according to the method of Example 6, except that n-butyl chloroformate was substituted for di-t-butyl dicarbonate, and the overnight reaction was conducted at 50° C. The crude product was purified by reverse phase HPLC, as described in Example 6, to give a 30% yield of the title compound as a nearly white solid; homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 694 (M+1)+. 400 MHz 1H NMR (CDCl3) δ0.81 (t, J=7.4 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H), 1.15 (m, 2H), overlapping 1.21 (t, J=7.5 Hz, 3H), 1.38-1.46 (m, 2H), 1.72 (m, 2H), 2.38 (q, J=7.5 Hz, 2H), 2.74 (t, J=7.8 Hz, 2H), 3.97 (t, J=6.5 Hz, 2H), overlapping 4.04 (br s, 2H), 7.06-7.12 (m, 2H), 7.27-7.35 (m, 2H), 7.40-7.68 (m, 5H), 7.97 (s, 1H), 8.26 (dd, J=8.0, 1.3 Hz, 1H).

後処理

  1. customthe overnight reaction
  2. customwas conducted at 50° C
  3. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-8d850055b93c48f39bd10f93b5715dc2
出典データセット
uspto-grants-1993_11
特許番号
US05262412

関連ノート

読み込み中…