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

HRID 229633

반응식

HRID 229633 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5d5d12ad226c4d1799c067c1d4555aac
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563791B2

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