Cesium carbonate → 5-[4-(6-Fluoro-benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amide

HRID 1799081ノート

反応式

HRID 1799081 の反応式
Cl[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:5][CH:4]=1.Cl.[CH2:21]1[CH:25]2[CH2:26][NH:27][CH2:28][CH:24]2[CH2:23][N:22]1[C:29]([NH2:31])=[O:30].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([O:7][C:6]3[CH:18]=[CH:19][C:3]([CH2:2][N:27]4[CH2:26][CH:25]5[CH2:21][N:22]([C:29]([NH2:31])=[O:30])[CH2:23][CH:24]5[CH2:28]4)=[CH:4][CH:5]=3)[S:9][C:10]=2[CH:16]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 57448388Hexahydropyrrolo[3,4-c]pyrrole-2(1h)-carboxamide hydrochlorideHCID 672062122-(4-Chloromethyl-phenoxy)-6-fluoro-benzothiazole

生成物 1

HCID 425974195-[4-(6-Fluoro-benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amide収率 7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 2-(4-chloromethyl-phenoxy)-6-fluoro-benzothiazole (152 mg, 0.52 mmol), hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amide hydrochloride (110 mg, 0.57 mmol) and Cs2CO3 (676 mg, 2.08 mmol) in DMF (1 mL) was stirred at rt overnight. The resultant mixture was filtered and the residue purified via preparative reverse phase HPLC to afford the title compound (15 mg, 7%). MS (ESI): Mass calcd for C21H21N4O2SF, 412.1; m/z found, 413.1 [M+H]+; 1H NMR (400 MHz, CD3OD): 7.64 (dd, J=8.9, 4.7 Hz, 1H), 7.58 (dd, J=8.4, 2.6 Hz, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 7.19 (dt, J=9.0, 8.9, 2.6 Hz, 1H), 3.66 (s, 2H), 3.59-3.40 (m, 2H), 3.29-3.27 (m, 2H), 2.97-2.83 (m, 2H), 2.77 (d, J=9.3, 6.8 Hz, 2H), 2.46 (d, J=9.3, 3.6 Hz, 2H).

後処理

  1. filtrationThe resultant mixture was filtered
  2. customthe residue purified via preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-8694053749ff42c58991470d8f42901a
出典データセット
uspto-grants-2013_01
特許番号
US08344008B2

反応ノート

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