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Diisopropylethylamine → 3-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-one

HRID 1081516
ノート
印刷プレビュー

反応式

HRID 1081516 の反応式
[CH2:1]([O:3][C:4]1[CH:33]=[CH:32][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=O)=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].[CH3:34][N:35]([CH3:41])[CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:11]1([N:10]2[C:6]3[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:33]=[CH:32][C:7]=3[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:29])[NH:40][C:37]([CH3:39])([CH3:38])[CH2:36][N:35]([CH3:41])[CH3:34])=[CH:23][C:22]=3[O:30][CH3:31])(=[O:19])=[O:20])[C:9]2=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 226843(2-Amino-2-methylpropyl)dimethylamineHCID 152290425-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

生成物 1

HCID 23364231
3-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-one
収率 53.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1 g of the compound obtained in EXAMPLE 13, 1 g of 2-dimethylamino -1,1- dimethylethylamine (synthesized according to J. Am. Chem. Soc., 1946, 68, 10-12), 1 g of BOP, 1 ml of DIPEA and 20 ml of DCM is stirred for 16 hours at RT. The reaction mixture is evaporated under vacuum, the residue is extracted with AcOEt, washed with a 1N solution of NaOH, extracted with a 6N solution of HCl, washed with AcOEt, the acidic aqueous phase is rendered alkaline by the addition of 2N NaOH, extracted with AcOEt and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/MeOH mixture (99/1; v/v) as the eluent to give 0.65 g of the expected product after crystallization from iso ether. M.p.=161° C.

後処理

  1. customThe reaction mixture is evaporated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washwashed with a 1N solution of NaOH
  4. extractionextracted with a 6N solution of HCl
  5. washwashed with AcOEt
  6. additionby the addition of 2N NaOH
  7. extractionextracted with AcOEt
  8. dry with materialdried over Na2SO4
  9. customthe solvent is evaporated off under vacuum
  10. customThe residue is chromatographed on silica using a DCM/MeOH mixture (99/1; v/v) as the eluent

出典と根拠

ORDレコード
ord-a22e3644e0034c9ba4f7b23107f49fd2
出典データセット
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05585394

反応ノート

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