Dimethylformamide → HCID 86683409, compound

HRID 579433Notes

Reaction equation

HRID 579433 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[C:5]=1[CH:14]=[O:15].CN(C)C=O.Cl[C:22]1[S:23][C:24]([C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[O:29])=[C:25]([CH3:27])[N:26]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:2][O:3][C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][N:9]([C:22]3[S:23][C:24]([C:28]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[O:29])=[C:25]([CH3:27])[N:26]=3)[CH2:8][CH2:7][C:6]=2[C:5]=1[CH:14]=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 67447923HCID 67447923, compoundHCID 86683400HCID 86683400, compound

Product 1

HCID 86683409HCID 86683409, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0.11999999731779099 °C

Procedure

A mixture of 6-methoxy-1,2,3,4-tetrahydro-isoquinoline-5-carbaldehyde hydrochloride (82 mg, 0.36 mmol), anhydrous dimethylformamide (5 mL), (2-chloro-4-methyl-thiazol-5-yl)-morpholin-4-yl-methanone (89 mg, 0.36 mmol) and freshly dried potassium carbonate (149 mg, 1.08 mmol) was stirred under argon at 0.120° C. for 3.5 h and then at 150° C. for 1 h. Water (20 mL) was added and the separated solid product was filtered off. The filtrate was extracted with diethyl ether (5×10 mL) and the combined extracts were washed with water (2×10 mL), dried and concentrated. The residue and the above solid product were combined and triturated repeatedly with diisopropyl ether. In this manner the title compound (37 mg, 0.092 mmol, 26%) was obtained as a beige powder.

Workup

  1. waitat 150° C. for 1 h
  2. filtrationthe separated solid product was filtered off
  3. extractionThe filtrate was extracted with diethyl ether (5×10 mL)
  4. washthe combined extracts were washed with water (2×10 mL)
  5. customdried
  6. concentrationconcentrated
  7. customtriturated repeatedly with diisopropyl ether

Sources & evidence

ORD record
ord-c1eda36c53ce489cb3a4c2fc9b353d87
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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