Methanol → HCID 70557102, compound

HRID 1503870Notes

Reaction equation

HRID 1503870 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=O)=[CH:4][C:3]=1[O:15][CH3:16].CO>O1CCCC1>[CH3:16][O:15][C:3]1[CH:4]=[C:5]([CH2:8][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 67159457HCID 67159457, compound

Product 1

HCID 70557102HCID 70557102, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the product of Example 49A (220 mg, 3.64 mmol) in tetrahydrofuran (20 mL) at 0° C. was added borane tetrahydrofuran complex (18 mL, 18 mmol) and the mixture was stirred at 0° C. for 2 hours and at 60° C. for 4 hours. After cooling to ambient temperature, methanol (20 mL) was added and stirring was continued for 30 minutes. The organic phase was concentrated and the residue was purified via preparative HPLC using a gradient of 10/90 to 80/20 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. MS: 207 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. concentrationThe organic phase was concentrated
  5. customthe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-6bd0e0b12904430da8f0b3309d4f6760
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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