HCID 72567245, compound → HCID 59807061, compound

HRID 1922437Notes

Reaction equation

HRID 1922437 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[C:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]1)([O-])=O>N.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]2[CH:14]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]1

Participants

5

Reactant 1

HCID 72567245HCID 72567245, compound

Product 1

HCID 59807061HCID 59807061, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of compound 2 (0.3 g, 0.868 mmol) in 7 N NH3 in methanol (10 mL) was treated with Pd—C (˜0.03 g) and purged with hydrogen gas. The reaction was stirred at room temperature under hydrogen atm. (balloon pressure) for 3 h. The reaction was filtered through celite bed, washed with methanol (3×10 mL). The combined organic layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 3 (0.25 g, 91%) as a solid. 1H NMR (DMSO-d6) δ 9.99 (s, 1H), 6.57-6.50 (m, 2H), 6.39 (d, 1H, J=8.7 Hz), 4.69 (d, 2H, J=4.2 Hz), 3.56-3.35 (m, 3H), 3.15-3.04 (m, 2H), 2.50-2.49 (m, 1H), 1.98-1.66 (m, 2H), 1.37 (s, 9H); ESI-MS (m/z, %): 340 (M+Na, 5), 244 (100), 218 (MH+-Boc, 84).

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with methanol (3×10 mL)
  4. customThe combined organic layer was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-916193b232d24a31a373c041ef0ddff3
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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