Formic Acid → HCID 87205335, compound

HRID 1364575Notes

Reaction equation

HRID 1364575 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#N)=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[O:14])[CH:3]=1.C(O)=[O:28]>>[NH2:1][C:2]1[C:7]([CH:8]=[O:28])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[O:14])[CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 11846124HCID 11846124, compound

Product 1

HCID 87205335HCID 87205335, compoundYield 36%

Procedure

To a suspension of Example 176 (73 mg, 0.2 mmol) in HCOOH (5 ml, 98%) was added AlNi3 (84 mg, 0.6 mmol). The mixture was refluxed for overnight and filtered after cooled down to r.t. The filtrate was concentrated and the remainder was purified on HPLC (10 mM ammonium acetate, 5% acetonitrile in H2O/CH3CN) to yield the titled compound (25 mg, 36%). 1H NMR (300 MHz, DMSO-d6) δ 10.23 (s, 1H), 9.20 (t, J=6.44 Hz, 1H) 8.46 (s, 1H), 7.95 (s, 1H), 7.88 (d, J=8.48 Hz, 1H), 7.55 (d, J=8.48 Hz, 2H), 7.08 (s, 1H) 4.57 (d, J=8.48 Hz, 2H), 4.54 (d, J=6.44 Hz, 2H), 3.18 (s, 3H), 1.35 (q, J=6.44 Hz, 3H); MS (APCI) m/z 378 [M+H]+, 376 [M−H]−.

Workup

  1. temperatureThe mixture was refluxed for overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe remainder was purified on HPLC (10 mM ammonium acetate, 5% acetonitrile in H2O/CH3CN)

Sources & evidence

ORD record
ord-347525f9b27f4d439e014633704ef82f
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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