Water → HCID 68183027, compound

HRID 1615561Notes

Reaction equation

HRID 1615561 reaction equation
[CH2:1]([C:4]1([C:28]([O:30]C)=[O:29])[NH:9][C:8](=[O:10])[C:7]2[S:11][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:13][C:6]=2[CH:5]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[CH:2]=[CH2:3].[OH-].[Na+].O>CO.O1CCCC1>[CH2:1]([C:4]1([C:28]([OH:30])=[O:29])[NH:9][C:8](=[O:10])[C:7]2[S:11][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:13][C:6]=2[CH:5]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 962Water2×HCID 14798Sodium Hydroxide2×HCID 68183034HCID 68183034, compound

Product 1

HCID 68183027HCID 68183027, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 5-allyl-4-(3,4-dichlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylate (0.118 g, 0.245 mmol), methanol (2.0 mL), tetrahydrofuran (2.0 mL) and a solution of 1.0 M sodium hydroxide in water (1.50 mL, 1.50 mmol) was stirred at rt overnight. Additional methanol (2.0 mL) and 1.0 M Sodium hydroxide in water (1.50 mL, 1.50 mmol) was added. The mixture was stirred at rt for 2 days. The mixture was concentrated to remove most of volatile solvents and then acidified by 1M HCl. The precipitate was collected and dried in air to afford crude product. Final purification by HPLC afforded pure product as a white solid (43.3 mg, 23%). LCMS (FA) ES+: 467, 469. 1H NMR (400 MHz, DMSO) δ 7.45 (d, J=8.3 Hz, 1H), 7.38 (s, 1H), 7.25 (br s, 1H), 7.12 (d, J=8.2 Hz, 1H), 6.50 (s, 1H), 6.04 (s, 1H), 5.74-5.63 (m, 1H), 4.99-4.89 (m, 2H), 4.18 (s, 1H), 3.68 (br s, 4H), 3.12 (br s, 4H), 2.54-2.50 (m, 2H, overlapping with DMSO peak).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove most of volatile solvents
  3. customThe precipitate was collected
  4. customdried in air
  5. customto afford crude product
  6. customFinal purification by HPLC

Sources & evidence

ORD record
ord-a2ef14b21d934ecc9ea2a7caea7d4f6a
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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