Fumaric Acid → HCID 86646955, compound

HRID 1096480Notes

Reaction equation

HRID 1096480 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=4)=[C:21]([F:36])[CH:20]=3)[C:9]([C:11]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>C1COCC1>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[NH2:1][C:2]1[C:7]2=[C:8]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=4)=[C:21]([F:36])[CH:20]=3)[C:9]([C:11]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 42597459HCID 42597459, compound

Product 1

HCID 86646955HCID 86646955, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-amino-5-(3-fluoro-4-{[(6-methylpyridin-2-yl)carbamoyl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide (8.0 g) in THF (800 mL) was heated until dissolution took place (up to 80° C.). The reaction mixture was cooled to it and fumaric acid (1.38 g, 11.9 mmol) was added. The mixture was left to stir for 16 h. The solid was filtered using a 0.2 uM membrane filter. The solid was dried to give 6.35 g (71%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 9.95 (s, 1H), 8.68 (t, 1H), 8.35 (t, 1H), 8.23 (s, 1H), 7.95 (s, 1H), 7.65 (t, 1H), 7.32 (d, 1H), 7.17 (d, 1H), 7.05 (bd, 1H), 6.95 (d, 1H), 6.61 (s, 1H), 3.98 (m, 2H), 2.54 (s, 3H); ES-MS m/z 503.30 (MH)+, HPLC RT (Method A) 2.63 min. DSC mp.=229.54° C. Anal. Calc'd for C22H18F4N8O2.0.5(C4H4O4): C, 51.43%; H, 3.60%; F, 13.56%; N, 19.99%; O, 11.42%; Found: C, 50.90%; H, 3.78%; N, 19.67%.

Workup

  1. customup to 80° C.
  2. additionwas added
  3. waitThe mixture was left
  4. filtrationThe solid was filtered
  5. filtrationfilter
  6. customThe solid was dried

Sources & evidence

ORD record
ord-6a1f68b0382c4030ba1b7bde2a171b28
Source dataset
uspto-grants-2012_03
Patent number
US08138336B2

Reaction notes

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