Hydrochloric Acid → HCID 21082488, compound

HRID 347340Notes

Reaction equation

HRID 347340 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:18]=[C:17]([CH3:19])[O:16][N:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:20][O:21][C:22]1[C:29]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)=[CH:28][C:25]([CH:26]=O)=[C:24]([O:35][CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH:23]=1.C[O-].[Li+].[ClH:47]>CN(C)C=O.CO.O>[ClH:47].[CH3:20][O:21][C:22]1[C:29]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)=[CH:28][C:25](/[CH:26]=[CH:2]/[C:1]([C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]3[CH:18]=[C:17]([CH3:19])[O:16][N:15]=3)(=[O:11])=[O:12])=[CH:8][CH:9]=2)=[O:3])=[C:24]([O:35][CH2:36][CH2:37][N:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)[CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4177230Lithium methanolateHCID 85190264-acetyl-N-(5-methylisoxazole-3-yl)benzenesulfonamideHCID 161161844-Methoxy-2-(2-morpholin-4-ylethoxy)-5-thien-2-ylbenzaldehyde

Product 1

HCID 21082488HCID 21082488, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

4-Acetyl-N-(5-methylisoxazole-3-yl)benzenesulfonamide (Ex-1B, 0.30 g, 0.86 mmol) and 4-methoxy-2-(2-morpholin-4-ylethoxy)-5-thien-2-ylbenzaldehyde (Ex-14A, 0.24 g, 0.86 mmol) were dissolved in a dimethylformamide-methanol solution (6.0 mL, 7:3). After complete dissolution, lithium methoxide (0.13 g, 3.4 mmol) was added and the resulting orange slurry was stirred in the dark at room temperature for 1 h. Upon completion, as determined by HPLC, the mixture was diluted with water (8.0 mL), acidified with a 1 N hydrochloric acid solution, and extracted with ethyl acetate:tetrahydrofuran (1:1, 3×20 mL). The combined organic extracts were evaporated to dryness. The crude oil was taken up in ethanol (10 mL) and warmed to 60° C. to obtain complete dissolution and allowed to cool to room temperature. The resulting precipitate was collected on filter paper and dried in vacuo to yield 0.46 g (88%) of the title compound as a pale orange solid, mp>260° C. 1H-NMR (300 MHz, DMSO-d6) 8.34 (d, 2H, J=9.0 Hz), 8.32 (s, 1H), 8.12 (d, 1H, J=15.9 Hz), 8.03 (d, 2H, J=9.0 Hz), 7.93 (d, 1H, J=15.9 Hz), 7.69 (d, 1H, J=3.3 Hz), 7.56 (d, 1H, J=5.4 Hz), 7.15 (dd, 1H, J=5.4, 3.3 Hz), 6.92 (s, 1H), 6.18 (s, 1H), 4.65 (brs, 2H), 4.03 (s, 3H), 3.97 (brs, 4H), 3.69 (brs, 2H), 3.50–3.23 (brs, 4H), 2.31 (s, 3H). Anal. Calcd. for C30H32ClN3O7S2.H2O: C, 54.25; H, 5.16; N, 6.33; S, 9.66; Found: C, 54.10; H, 4.91; N, 6.39; S, 9.68. HRMS (ESI) Calcd. for C30H32ClN3O7S2: 610.1681 (—HCl) (M+H)+. Found: 610.1673.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate:tetrahydrofuran (1:1, 3×20 mL)
  3. customThe combined organic extracts were evaporated to dryness
  4. temperaturewarmed to 60° C.
  5. customto obtain complete
  6. dissolutiondissolution
  7. temperatureto cool to room temperature
  8. customThe resulting precipitate was collected
  9. filtrationon filter paper
  10. customdried in vacuo

Sources & evidence

ORD record
ord-3bd442557b4f49ed98b0e4c02bd86540
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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