Formic Acid → HCID 57503317, compound

HRID 916673Notes

Reaction equation

HRID 916673 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([C:20](=O)[CH3:21])[C:15]=3[CH2:23][CH2:24][CH3:25])[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:4][CH:3]=1.C(O)=O.[CH:29]([NH2:31])=[O:30].[OH-].[Na+]>O>[F:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([CH:20]([NH:31][CH:29]=[O:30])[CH3:21])[C:15]=3[CH2:23][CH2:24][CH3:25])[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 284Formic Acid2×HCID 713FormamideHCID 14798Sodium HydroxideHCID 57503316HCID 57503316, compound

Product 1

HCID 57503317HCID 57503317, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

214 (0.1 g) and formic acid (0.1 mL) are added to 2 mL of formamide at 160–180° C. The mixture is heated at 160–180° C. for an additional 3 hours. During this period, additional formic acid (0.2 mL) is added. The mixture is cooled to room temperature and poured into water (10 mL). The solution is made alkaline to at least pH 11 with concentrated sodium hydroxide. The solution is extracted with ethyl acetate. The combined organic layers are dried over MgSO4, and the solvent is removed to give the crude product. PTLC separation with 10% MeOH in methylene chloride gives the title product (215). 1H NMR δ (CDCL3) 1.06 (t, 3H, J=7.5 Hz), 1.43 (d, 3H, J=5.1 Hz), 1.55 –1.72 (m, 2H), 2.72–2.80 (m, 1H), 2.86–2.95 (m, 1H), 5.52 (p, 1H, J=5.4 Hz), 5.81 (d, 1H, J=12.3 Hz), 6.08 (d, 1H, J=12.3 Hz), 6.73 (dd, 1 H, J=6, 2.1 Hz)), 6.99 (d, 1H, J=5.7 Hz), 7.12 (d, 1H, J=2.7 Hz), 7.23 (d, 1H, J=2.7 Hz), 7.78 (q, 1H, J=6.0 Hz), 8.12 (dd, 1H, J=6.0, 2.1 Hz), 8.18 (s, 1H), 8.79 (s, 1H). LC-MS: (M+1) 369.13.

Workup

  1. temperatureThe mixture is heated at 160–180° C. for an additional 3 hours
  2. waitDuring this period
  3. extractionThe solution is extracted with ethyl acetate
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. customthe solvent is removed
  6. customto give the crude product
  7. customPTLC separation with 10% MeOH in methylene chloride

Sources & evidence

ORD record
ord-c1a8ea2ca31641aa804b1dd80a482fa8
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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