Methanol → HCID 57509940, compound

HRID 624122Notes

Reaction equation

HRID 624122 reaction equation
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:28](O)=[O:29])[CH:25]=4)[CH2:20]3)=[O:18])=[CH:12][CH:11]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.B.CO>O1CCCC1.Cl.O1CCOCC1>[CH:1]1([CH2:6][CH2:7][NH:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([N:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:28][OH:29])[CH:25]=4)[CH2:20]3)=[O:18])=[CH:14][CH:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 57509938HCID 57509938, compound

Product 1

HCID 57509940HCID 57509940, compound

Reagents, catalysts & solvents 2

HCID 204431481,4-Dioxane hydrochlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirring suspension of 2-(4-(2-cyclopentylacetamido)phenylcarbamoyl)isoindoline-5-carboxylic acid (18 mg, 0.044 mmol) in tetrahydrofuran was added 1M borane in tetrahydrofuran (0.18 mL, 0.18 mml) dropwise. The mixture was heated at 60° C. for 1 hour. The reaction was cooled to room temperature and treated with several drops of 4M HCl-dioxane and methanol and then the clear solution was stirred at room temperature for 2 hours. The reaction was concentrated and purified by reverse-phase HPLC to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.92 (s, 1H), 7.27-7.31 (m, 2H), 7.24 (d, J=8.1 Hz, 1H), 7.15-7.20 (m, 2H), 6.45-6.51 (m, 2H), 5.17-5.21 (m, 2H), 4.68-4.69 (bs, 4H), 4.51 (d, J=5.4 Hz, 2H), 2.97 (q, J=6.7 Hz, 2H), 1.70-1.95 (m, 3H), 1.42-1.66 (m, 6H), 1.04-1.20 (m, 2H); MS (ESI(+)) m/e 380 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationThe reaction was concentrated
  3. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-2e810da0b48b4424878e6ef060adc888
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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