Methanesulfonic Acid → 5-(4-Nitro-phenyl)-6-oxazol-2-yl-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

HRID 229633

反応式

HRID 229633 の反応式
Cl.FC(F)(F)CN.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CO[CH:29]([O:53]C)[CH2:30][NH:31][C:32]([C:34]1[C:35]([C:44]2[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=2)=[C:36]2[N:41]([CH:42]=1)[N:40]=[CH:39][N:38]=[C:37]2[NH2:43])=O.C(=O)([O-])[O-].[Na+].[Na+]>>[N+:50]([C:47]1[CH:48]=[CH:49][C:44]([C:35]2[C:34]([C:32]3[O:53][CH:29]=[CH:30][N:31]=3)=[CH:42][N:41]3[C:36]=2[C:37]([NH2:43])=[N:38][CH:39]=[N:40]3)=[CH:45][CH:46]=1)([O-:52])=[O:51]

参加物

6

反応物 5

HCID 6395Methanesulfonic AcidHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 10340Sodium CarbonateHCID 14812Phosphorus oxide (P4O10)HCID 866148604-Amino-5-(4-nitro-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (2,2-dimethoxy-ethyl)-amide

生成物 1

HCID 577580655-(4-Nitro-phenyl)-6-oxazol-2-yl-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

反応条件

温度
100 °C

実験手順

The procedure used for the preparation of the first step of intermediate M was used to prepare 4-Amino-5-(4-nitro-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (2,2-dimethoxy-ethyl)-amideby substituting 2,2-Dimethoxy-ethylamine for 2,2,2-trifluoro-ethylamine hydrochloride salt. To a solution of methanesulfonic acid (1.5 ml) was added P2O5 (225.0 mg, 1.58 mmol) followed by the addition of 4-amino-5-(4-nitro-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid (2,2-dimethoxy-ethyl)-amide (150 mg, 0.388 mmol). The dark brown mixture was heated to 100° C. and allowed to stir for 18 hrs. The mixture was then poured over ice (15 g), stirred for fifteen minutes and enough saturated sodium carbonate solution was added to neutralize the reaction. A white precipitate was filtered and collected (35 mg, 27%). 1H-NMR (DMSO-d6)δ 8.33 (s, 1H), 8.31 (m, 2H), 8.03 (d, J=10 Hz, 2H), 7.73 (d, J=10 Hz, 2H), 7.28 (s, 1H). MS [M+H]+=323.2; LCMS RT=2.51 min.

後処理

  1. stirringstirred for fifteen minutes
  2. customthe reaction
  3. filtrationA white precipitate was filtered
  4. customcollected (35 mg, 27%)

出典と根拠

ORDレコード
ord-5d5d12ad226c4d1799c067c1d4555aac
出典データセット
uspto-grants-2009_07
特許番号
US07563791B2

関連ノート

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