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

HRID 2198085Notes

Reaction equation

HRID 2198085 reaction equation
CO[CH:3]([O:27]C)[CH2:4][NH:5][C:6]([C:8]1[C:9]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[C:10]2[N:15]([CH:16]=1)[N:14]=[CH:13][N:12]=[C:11]2[NH2:17])=O.Cl.FC(F)(F)CN.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([C:9]2[C:8]([C:6]3[O:27][CH:3]=[CH:4][N:5]=3)=[CH:16][N:15]3[C:10]=2[C:11]([NH2:17])=[N:12][CH:13]=[N:14]3)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

6

Reactant 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)-amide2×

Product 1

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

Conditions

Temperature
100 °C

Procedure

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)-amide by 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.

Workup

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

Sources & evidence

ORD record
ord-f5105cf8e4564f9aa1780385ae86ddc6
Source dataset
uspto-grants-2012_12
Patent number
US08338595B2

Reaction notes

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