1-Aminocyclobutanecarboxylic acid → (E)-3-[2-(1-aminocyclobutyl)-1-methyl-1H-benzoimidazol-5-yl]acrylic acid methyl ester

HRID 1360629ノート

反応式

HRID 1360629 の反応式
[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[C:8]([NH2:14])[CH:7]=1.[NH2:16][C:17]1([C:21](O)=O)[CH2:20][CH2:19][CH2:18]1>C(Cl)Cl.Cl.NC1(C(Cl)=O)CCC1.C(O)(=O)C.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]2[N:12]([CH3:13])[C:21]([C:17]3([NH2:16])[CH2:18][CH2:19][CH2:20]3)=[N:14][C:8]=2[CH:7]=1

参加物

7

反応物 2

HCID 896431-Aminocyclobutanecarboxylic acidHCID 58866234(E)-3-(3-amino-4-methylaminophenyl)acrylic acid methyl ester

生成物 1

HCID 58866235(E)-3-[2-(1-aminocyclobutyl)-1-methyl-1H-benzoimidazol-5-yl]acrylic acid methyl ester

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒HCID 21105264Cyclobutanecarbonyl chloride, 1-amino-, hydrochloride溶媒

実験手順

(E)-3-(3-Amino-4-methylaminophenyl)acrylic acid methyl ester 2-4 from Example 2 (40 mg, 0.194 mmol) was suspended in CH2Cl2 (3 mL) and 1-aminocyclobutanecarboxylic acid chloride hydrochloride, prepared from 1-aminocyclobutanecarboxylic acid following an adaptation of the procedure described by E. S. Uffelman et al. (Org. Lett. 1999, 1, 1157), (31 mg, 0.18 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours and then concentrated to obtain a white solid. The solid was then dissolved in acetic acid (5 mL) and heated to 60° C. for 20 hours. The reaction crude was diluted with aqueous saturated NaHCO3, extracted with CH2Cl2 (2×50 mL) and brine, the organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to give (E)-3-[2-(1-aminocyclobutyl)-1-methyl-1H-benzoimidazol-5-yl]acrylic acid methyl ester 3-1 as a light brown foam (53 mg).

後処理

  1. additionUffelman et al. (Org. Lett. 1999, 1, 1157), (31 mg, 0.18 mmol) was added
  2. concentrationconcentrated
  3. customto obtain a white solid
  4. temperatureheated to 60° C. for 20 hours
  5. customThe reaction crude
  6. extractionextracted with CH2Cl2 (2×50 mL) and brine
  7. dry with materialthe organic layer was dried over anhydrous MgSO4
  8. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-82aa502f6a3c490997c19d0e89b00239
出典データセット
uspto-grants-2011_02
特許番号
US07879851B2

反応ノート

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