HCID 58300017, compound → HCID 58300136, compound

HRID 876061Notes

Reaction equation

HRID 876061 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[CH:20][C:19]([C:22]5[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:28]=[CH:29][N:30]=[CH:31][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([CH:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:20][N:21]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:28]=[CH:29][N:30]=[CH:31][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 58300017HCID 58300017, compound

Product 1

HCID 58300136HCID 58300136, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 412 (90 mg, 0.22 mmol) in methanol (5 mL) was added Pd/C (10% wt, dry basis) (50 mg). The reaction was stirred at room temperature with H2 ballon for 3 hours. Insolubles were removed by filtration. The filtrate was purified using prep-HPLC to give compound 413 as a yellow solid (30 mg, 33%). 1H NMR (500 MHz, DMSO-d6) δ ppm 10.98 (1 H, br. s.), 9.64 (1 H, s), 9.42 (1 H, s), 8.83 (1 H, dd, J=3.5, 1.1 Hz), 8.71 (1 H, d, J=6.1 Hz), 8.55-8.68 (2 H, m), 8.30 (1 H, d, J=2.7 Hz), 8.17 (1 H, d, J=8.6 Hz), 7.85 (1 H, dd, J=8.8, 2.4 Hz), 5.41 (1 H, dq, J=8.9, 8.8 Hz), 3.43 (2 H, dd, J=10.4, 2.3 Hz), 2.96 (3 H, tt, J=12.1, 3.7 Hz), 2.42 (2 H, m), 2.00-2.08 (4 H, m), 1.68-1.92 (2 H, m); LCMS-ESI (POS), M/Z, M+1: Found 414.2, Calculated 414.2.

Workup

  1. customInsolubles were removed by filtration
  2. customThe filtrate was purified

Sources & evidence

ORD record
ord-ee1bc48d35d64b5f9441ca6c4405847b
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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