Methanol → HCID 67303914, compound

HRID 1008955Notes

Reaction equation

HRID 1008955 reaction equation
[CH2:1]([O:3][CH:4]([O:25][CH2:26][CH3:27])[CH2:5][CH2:6][NH:7][C:8]([NH:19][C:20]1[CH:24]=[CH:23][S:22][CH:21]=1)=[C:9]1[C:14](=[O:15])OC(C)(C)[O:11][C:10]1=[O:18])[CH3:2].C[Si](C)(C)N[Si](C)(C)C.CO>C(OCC)C>[CH2:26]([O:25][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][NH:7][C:8]1[NH:19][C:20]2[CH:24]=[CH:23][S:22][C:21]=2[C:14](=[O:15])[C:9]=1[C:10]([OH:11])=[O:18])[CH3:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 13838HexamethyldisilazaneHCID 67304186HCID 67304186, compound

Product 1

HCID 67303914HCID 67303914, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-((3,3-Diethoxypropylamino)(thiophene-3-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.62 mol) was suspended in a solution of hexamethyldisilazane (1.08 L, 5.18 mol) in xylenes (2.4 L) and was heated at reflux for 24 h. After cooling to room temperature, the mixture was concentrated under reduced pressure to afford a dark oil. The dark oil was carefully treated with methanol (0.5 L) to form brown solids, followed by addition of ethyl ether (1.6 L). The resultant solids were filtered and washed with MeOH/Ether (1:3) (0.8 L). The solids were dried under vacuum to afford 432.2 g (78%) of the desired intermediate 5-(3,3-Diethoxypropylamino)-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylic acid as a beige solid. 1H NMR (400 MHz, DMSO d6) δ 1.09 (m, 6H), 1.91 (m, 2H), 3.40 (m, 2H), 3.58 (m, 2H), 4.06 (s, 1H), 4.60 (t, 1H, J=5.2 Hz), 7.28 (d, 1H, J=4.8 Hz), 8.05 (d, 1H, J=4.8 Hz), 9.94 (m, 1H), 11.8 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customto afford a dark oil
  5. customto form brown solids
  6. filtrationThe resultant solids were filtered
  7. washwashed with MeOH/Ether (1:3) (0.8 L)
  8. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-85e30a7853eb4d329f78b6839953ea06
Source dataset
uspto-grants-2011_07
Patent number
US07973050B2

Reaction notes

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