Hydrochloric Acid → (Pyrrolidine-1-carbonyl)sulfamic acid 3-[3-tert-butyl-5-(3-naphthalen-1-yl-ureido)-pyrazol-1-yl]phenyl ester

HRID 16950

反応式

HRID 16950 の反応式
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[NH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[C:13]([C:17]1[CH:21]=[C:20]([NH:22][C:23]([NH:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)=[O:24])[N:19]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([OH:42])[CH:37]=2)[N:18]=1)([CH3:16])([CH3:15])[CH3:14].Cl.[Na+].[Cl-]>C(Cl)Cl>[C:13]([C:17]1[CH:21]=[C:20]([NH:22][C:23]([NH:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][CH:27]=2)=[O:24])[N:19]([C:36]2[CH:37]=[C:38]([O:42][S:2](=[O:4])(=[O:3])[NH:5][C:6]([N:8]3[CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])[CH:39]=[CH:40][CH:41]=2)[N:18]=1)([CH3:16])([CH3:14])[CH3:15]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 31268PyrrolidineHCID 70918Chlorosulfonyl isocyanateHCID 218673141-[3-Tert-butyl-1-(3-hydroxyphenyl)-1h-pyrazol-5-yl]-3-(naphthalene-1-yl)urea

生成物 1

HCID 25226698(Pyrrolidine-1-carbonyl)sulfamic acid 3-[3-tert-butyl-5-(3-naphthalen-1-yl-ureido)-pyrazol-1-yl]phenyl ester収率 1.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirring solution of chlorosulfonyl isocyanate (0.35 g, 5 mmol) in CH2Cl2 (20 mL) at 0° C. was added pyrrolidine (0.18 g, 5 mmol) at such a rate that the reaction temperature did not rise above 5° C. After stirring for 2 h, a solution of Example 41 (1.10 g, 6.5 mmol) and triethylmine (0.46 g, 9 mmol) in CH2Cl2 (20 mL) was added. When the addition was complete, the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was poured into 10% HCl (10 mL) saturated with NaCl, the organic layer was separated and the aqueous layer extracted with ether (20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo, purified by preparative HPLC to yield (pyrrolidine-1-carbonyl)sulfamic acid 3-[3-tert-butyl-5-(3-naphthalen-1-yl-ureido)-pyrazol-1-yl]phenyl ester (40 mg). 1H NMR (CDCl3): δ 9.12 (brs, 1H), 8.61 (brs, 1H), 7.85-7.80 (m, 3H), 7.65 (d, J=8.0 Hz, 2H), 7.53-7.51 (m, 1H), 7.45-7.25 (m, 5H), 6.89 (s, 4H), 3.36-3.34 (brs, 1H), 3.14-3.13 (brs, 2H), 1.69 (brs, 2H), 1.62 (brs, 2H), 1.39 (s, 9H); MS (ESI) m/z: 577 (M+H+).

後処理

  1. customdid not rise above 5° C
  2. additionWhen the addition
  3. stirringstirred overnight
  4. customthe organic layer was separated
  5. extractionthe aqueous layer extracted with ether (20 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-4004865e153a4770b4e3660e1db5d903
出典データセット
uspto-grants-2010_06
特許番号
US07737283B2

関連ノート

読み込み中…