3-[(2-Fluorophenyl)sulfamoyl]benzoic acid → N-(2-fluorophenyl)-3-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

HRID 1951488ノート

反応式

HRID 1951488 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([OH:17])=O)(=[O:11])=[O:10].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:45]1[NH:50][CH2:49][CH2:48][N:47]2[CH2:51][CH2:52][CH2:53][C@H:46]12>CN(C)C(=O)C.CC1CCCO1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([N:50]2[CH2:49][CH2:48][N:47]3[CH2:51][CH2:52][CH2:53][C@@H:46]3[CH2:45]2)=[O:17])[CH:13]=1)(=[O:10])=[O:11]

参加物

6

反応物 3

HCID 23180733-[(2-Fluorophenyl)sulfamoyl]benzoic acidHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 46853381N-(2-fluorophenyl)-3-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonamide

試薬・触媒・溶媒 2

HCID 73012-Methyltetrahydrofuran溶媒2 回HCID 31374Dimethylacetamide溶媒

実験手順

To a mixture of 3-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid (800 mg, 2.71 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (1133 mg, 2.98 mmol) in N,N-dimethylacetamide (6.5 mL) and 2-methyltetrahydrofuran (19.5 mL) was added (R)-octahydropyrrolo[1,2-α]pyrazine (479 mg, 3.79 mmol). The reaction was stirred at room temperature for 3 hours, diluted with 2-methyltetrahydrofuran (5 mL), and washed with saturated bicarbonate (2×25 mL). The combined aqueous layers were adjusted to pH 7 with buffer and re-extracted with 2-methyltetrahydrofuran (3×15 mL). The combined organic layers were concentrated under reduced pressure. The residue was taken up in ethanol (25 mL) and concentrated to give the title compound.

後処理

  1. washwashed with saturated bicarbonate (2×25 mL)
  2. extractionre-extracted with 2-methyltetrahydrofuran (3×15 mL)
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-561d5189ea4e45b694e1479698e5da8c
出典データセット
uspto-grants-2013_03
特許番号
US08404719B2

反応ノート

読み込み中…