Oxalic Acid → HCID 66786553, compound

HRID 1096481Notes

Reaction equation

HRID 1096481 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)[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:42])(=[O:41])[C:38]([OH:40])=[O:39]>C1COCC1>[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39].[NH2:1][C:2]1[C:7]2=[C:8]([C:19]3[CH:20]=[CH:21][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)=[CH:23][CH:24]=3)[C:9]([C:11]([NH:13][CH2:14][C:15]([F:18])([F:16])[F:17])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 42597459HCID 42597459, compound

Product 1

HCID 66786553HCID 66786553, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 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 (100 mg, 0.2 mmol) in THF (5 mL) was added 1M solution of oxalic acid (0.2 mL, 0.2 mmol, 225 mg was dissolved in 2.5 mL of THF to make a 1M solution) and the mixture was stirred at rt for 16 h. The solid was filtered using a 0.2 uM membrane filter, dried in high vacuum oven to give (60 mg, 51%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 9.95 (s, 1H), 8.60 (t, 1H), 8.36 (t, 1H), 8.21 (s, 1H), 7.94 (s, 1H), 7.66 (t, 1H), 7.30 (d, 1H), 7.11 (d, 1H), 6.96 (bd, 1H), 6.89 (d, 1H), 3.98 (m, 2H), 2.50 (s, 3H); ES-MS m/z 503.30 (MH)+, HPLC RT (Method A) 2.64 min. DSC mp.=210.36° C. Anal. Calcd for C22H18F4N8O2: C2H2O4: C, 48.66%; H, 3.40%; N, 18.91%. Found: C, 48.62%; H, 3.24%; N 18.69%.

Workup

  1. filtrationThe solid was filtered
  2. filtrationfilter
  3. customdried in high vacuum oven

Sources & evidence

ORD record
ord-e6ee293a3c6f4a058cd7d4c0b9d8d617
Source dataset
uspto-grants-2012_03
Patent number
US08138336B2

Reaction notes

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