HCID 59128671, compound → HCID 16064801, compound

HRID 1991126Notes

Reaction equation

HRID 1991126 reaction equation
[N:1]1([C:10]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C1COCC1>[N:1]1([CH2:10][C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 59128671HCID 59128671, compound

Product 1

HCID 16064801HCID 16064801, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1.0 M BH3 in THF (1.0 mL, 1.0 mmol) and amide 58 (80.7 mg, 0.235 mmol) in THF (2.0 mL) was refluxed under N2 for 20 min. The reaction mixture was cooled to r.t., quenched with MeOH (5 mL) and concentrated. The residual solid was treated with 10% aqueous HCl (2.0 mL) and MeOH (2.0 mL). After 1 h stirring at r.t. the mixture was concentrated, basified with NaHCO3 and extracted with AcOEt (3×10 mL). Combined extracts were dried (MgSO4), concentrated and purified by means of preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give 59 as a white solid (14.0 mg, 18%); 1H NMR (400 MHz, CDCl3) δ 2.97 (t, J=8.3 Hz, 2H), 3.30 (t, J=8.3 Hz, 2H), 3.98 (s, 3H), 4.40 (s, 2H), 6.66 (d, J=7.8 Hz, 1H), 6.72 (td, J=7.4, 0.8 Hz, 1H), 7.08-7.15 (m, 2H), 7.43 (d, J=1.6 Hz, 1H), 7.61 (s, 1H), 7.75 (s, 1H), 8.08 (d, J=1.8 Hz, 1H), 8.38 (d, J=1.8 Hz, 1H), 9.90 (bs, 1H).

Workup

  1. additionA mixture of 1.0 M
  2. customquenched with MeOH (5 mL)
  3. concentrationconcentrated
  4. additionThe residual solid was treated with 10% aqueous HCl (2.0 mL) and MeOH (2.0 mL)
  5. concentrationwas concentrated
  6. extractionextracted with AcOEt (3×10 mL)
  7. dry with materialCombined extracts were dried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by means of preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-e32ffd8f97324fdc8333f12a952cb46d
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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