Acetic Acid → HCID 57955273, compound

HRID 73715Notes

Reaction equation

HRID 73715 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=4)=[O:21])=[CH:15][CH:14]=3)[C:9]([CH:11]=[CH2:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.C(O)(=O)C>C1COCC1.CCO>[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=4)=[O:21])=[CH:15][CH:14]=3)[C:9]([CH2:11][CH3:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 577583301-[4-(4-Amino-6-vinylpyrrolo[2,1-f][1,2,4]triazin-5-yl)phenyl]-3-[4-(trifluoromethyl)pyridin-2-yl]urea

Product 1

HCID 57955273HCID 57955273, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[4-(4-amino-6-vinylpyrrolo[2,1-f][1,2,4]triazin-5-yl)phenyl]-3-[4-(trifluoro-methyl)pyridin-2-yl]urea (150 mg, 0.341 mmol) was slowly dissolved in THF (100 mL) by adding acetic acid (10-20 mL). The solution was further diluted with EtOH (300 mL) and run through the H-Cube® apparatus at 20 bar, rt, 1 mL/min. The resulting solution was concentrated then washed with satd. NaHCO3. A precititate formed and the desired product was collected by vacuum filtration to yield a tan solid. (150 mg, 99%). 1H-NMR (DMSO-d6) δ 11.89 (bs, 2H), 8.49 (d, J=5.0 Hz, 1H), 8.28 (s, 1H), 7.80 (s, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.60 (s, 1H), 7.27 (m, 3H), 2.48 (q, J=7.8 Hz, 2H), 1.09 (t, J=7.5 Hz, 3H). MS [M+H]+=442.0; LCMS RT=2.95.

Workup

  1. customrun through the H-Cube® apparatus at 20 bar, rt, 1 mL/min
  2. concentrationThe resulting solution was concentrated
  3. washthen washed with satd
  4. customA precititate formed
  5. filtrationthe desired product was collected by vacuum filtration
  6. customto yield a tan solid
  7. customLCMS RT=2.95

Sources & evidence

ORD record
ord-62e29bb6545e451c860859b84de447cd
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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