Formic Acid → 6-chloro-5-pyrrolidin-1-yl-1H-benzoimidazole

HRID 1521364

反応式

HRID 1521364 の反応式
[Cl:1][C:2]1[C:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][C:5]([NH2:13])=[C:4]([N+:14]([O-])=O)[CH:3]=1.Cl[Sn]Cl.O.[CH:21](O)=O>>[Cl:1][C:2]1[C:7]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][C:5]2[N:13]=[CH:21][NH:14][C:4]=2[CH:3]=1

参加物

4

反応物 3

HCID 284Formic AcidHCID 36137094-Chloro-2-nitro-5-(1-pyrrolidinyl)anilineHCID 43835034Tin dichloride dihydrate

生成物 1

HCID 669374346-chloro-5-pyrrolidin-1-yl-1H-benzoimidazole収率 70%

反応条件

温度
130 °C

実験手順

Formic acid (2.9 mL) was added to a mixture of 4-chloro-2-nitro-5-pyrrolidin-1-yl-phenylamine (0.240 g, 1.00 mmol) and SnCl2.H2O (0.680 g, 3.00 mmol), and the mixture was heated to 130° C. in a microwave reactor for 5 min. Six reactions were performed on the same scale. The combined crude mixture was filtered and washed with EtOAc (100 mL). The organic layer was treated with water (25 mL) and neutralized with aqueous 6M NaOH. The aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (50 mL), dried, filtered, and concentrated under reduced pressure. The residue was triturated with EtOAc and the solid was collected to yield the titled compound (1.08 g, 70%) as the formate salt. MS (ESI/CI): mass calcd. for C11H12ClN3, 221.1; m/z found, 222.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.84-12.16 (br s, 1H), 8.13 (s, 1H), 8.11 (s, 1H), 7.59 (s, 1H), 7.20 (s, 1H), 3.20 (t, J=6.3 Hz, 4H), 2.06-1.66 (m, 4H).

後処理

  1. filtrationwas filtered
  2. washwashed with EtOAc (100 mL)
  3. additionThe organic layer was treated with water (25 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
  5. washThe combined organic layers were washed with brine (50 mL)
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with EtOAc
  10. customthe solid was collected

出典と根拠

ORDレコード
ord-5c13cfe874614e8190e1e044b5b965ba
出典データセット
uspto-grants-2015_07
特許番号
US09073923B2

関連ノート

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