Iodine → 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrile

HRID 1969510ノート

反応式

HRID 1969510 の反応式
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([N:28]5[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29]5)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].II.[NH4+:37].[OH-]>C1COCC1.[O-]S([O-])=O.[Na+].[Na+].CCOC(C)=O>[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([N:28]5[CH:32]=[CH:31][C:30]([C:33]#[N:37])=[CH:29]5)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

参加物

7

反応物 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 866604291-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbaldehyde

生成物 1

HCID 679985851-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrile収率 101%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 24437Sodium Sulfite溶媒

実験手順

To a solution of 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbaldehyde (0.050 g, 0.105 mmol) in THF (2 mL) was added iodine (0.083 g, 0.327 mmol) and aqueous NH4OH (28-30% w/v, 0.733 mL, 5.27 mmol). The reaction mixture was stirred at ambient temperature for about 24 h. The reaction mixture was diluted with saturated aqueous Na2SO3 (30 mL) and EtOAc (30 mL). The layers were partitioned and the organic layer was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give 1-((1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-1H-pyrrole-3-carbonitrile (0.05 g, 100%): LC/MS (Table 1, Method a) Rt=2.33 min; MS m/z: 472 (M+H)+.

後処理

  1. customThe layers were partitioned
  2. dry with materialthe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-7b982bc9d2fe446eb1c1edb8730f7b86
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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