Sulfuric Acid → HCID 68751818, compound

HRID 624111Notes

Reaction equation

HRID 624111 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:26])[NH:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=1)=[O:13])[CH2:6]2)#[N:2].S(=O)(=O)(O)[OH:28]>FC(F)(F)C(O)=O>[CH2:23]([NH:22][C:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]([N:7]2[CH2:6][C:5]3[C:9](=[CH:10][CH:11]=[C:3]([C:1]([NH2:2])=[O:28])[CH:4]=3)[CH2:8]2)=[O:13])=[CH:16][CH:17]=1)=[O:26])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 57509632HCID 57509632, compound

Product 1

HCID 68751818HCID 68751818, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-cyano-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide (30 mg, 0.9 mmol) in sulfuric acid (0.1 mL) and trifluoroacetic acid (0.3 mL) was stirred at room temperature for 16 hours. The reaction was treated with ice and the suspension was stirred for 10 minutes and filtered. The solid collected was washed with water and dried under vacuum; the solid was purified by reverse-phase HPLC to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.61 (s, 1H), 8.26 (t, J=5.7 Hz, 1H), 7.97-8.00 (bs, 1H), 7.81-7.86 (m, 2H), 7.75-7.79 (m, 2H), 7.63-7.68 (m, 2H), 7.44 (d, J=7.8 Hz, 1H), 7.34-7.39 (bs, 1H), 4.81-4.82 (bs, 4H), 3.16-3.24 (m, 2H), 1.46-1.59 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 367 (M+H)+.

Workup

  1. additionThe reaction was treated with ice
  2. filtrationfiltered
  3. customThe solid collected
  4. washwas washed with water
  5. customdried under vacuum
  6. customthe solid was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-cc80e13a0d2042af85c7a81eabc7f71f
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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