Hydrochloric Acid → HCID 57510187, compound

HRID 624197Notes

Reaction equation

HRID 624197 reaction equation
[CH2:1]([N:8]([CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([N:20]2[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21]2)=[O:19])=[CH:13][CH:12]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.CO>[CH2:1]([N:8]([CH2:9][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([N:20]2[CH2:21][C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:28]2)=[O:19])=[CH:13][CH:12]=1)[CH2:29][CH2:30][CH2:31][N:32]1[CH2:33][CH2:34][O:35][CH2:36][CH2:37]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57510171HCID 57510171, compound

Product 1

HCID 57510187HCID 57510187, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring suspension of N-(4-{benzyl[3-(morpholin-4-yl)propyl]carbamoyl}phenyl)-1,3-dihydro-2H-isoindole-2-carboxamide (0.028 g, 0.056 mmol) in THF (1.1 ml) was added 1M borane tetrahydrofuran complex (0.225 ml, 0.225 mmol) dropwise. The mixture was heated at 60° C. for 5 hours. Additional borane complex (0.084 mL) was added and reaction was heated at 60° C. for 1 hour. The reaction was cooled to ambient temperature and 0.3 mL of 1.25 M HCl in methanol was added. The quenched reaction was stirred 30 min and concentrated. The title compound was isolated after flash chromatography. 1H NMR (400 MHz, pyridine-d5, Temp=90° C.) δ ppm 8.05 (s, 1H), 7.88-7.82 (m, 2H), 7.47-7.38 (m, 4H), 7.36-7.29 (m, 2H), 7.26-7.15 (m, 5H), 4.85 (bs, 4H), 3.68-3.59 (m, 8H), 3.48-3.35 (m, 1H), 2.59 (t, J=7.0 Hz, 2H), 2.38-2.29 (m, 6H), 1.79-1.65 (m, 3H); MS (ESI(+)) m/e 485 (M+H)+.

Workup

  1. additionwas added 1M borane tetrahydrofuran complex (0.225 ml, 0.225 mmol) dropwise
  2. additionAdditional borane complex (0.084 mL) was added
  3. customreaction
  4. temperaturewas heated at 60° C. for 1 hour
  5. temperatureThe reaction was cooled to ambient temperature
  6. customThe quenched reaction
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fb9af0d368514517ad4799f7f67c2dc6
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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