Dichloromethane → HCID 5276323, compound

HRID 2307288Notes

Reaction equation

HRID 2307288 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:19]=[C:18]([CH2:20]Cl)[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:34]1([CH2:40][C@H:41]2[CH2:46][O:45][CH2:44][CH2:43][NH:42]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(Cl)Cl>CN(C=O)C>[CH2:40]([C@H:41]1[CH2:46][O:45][CH2:44][CH2:43][N:42]1[CH2:20][C:18]1[S:17][C:13]2[N:14]([CH3:16])[CH:15]=[C:10]([C:8]([NH:7][CH2:6][C:5]3[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])[C:11](=[O:22])[C:12]=2[CH:19]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 10249252HCID 10249252, compoundHCID 10487535(S)-3-Benzylmorpholine

Product 1

HCID 5276323HCID 5276323, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Preparation 1, 100 mg) and diisopropylethylamine (0.13 mL) is added to a mixture of (S)-3-(phenylmethyl)morpholine (93 mg, prepared as described by Shawe, T. T. Syn. Comm. 1997,27,1777-1782) in DMF (5 mL). The mixture is heated at 90° C. for 3 hours. After cooling to room temperature, the solution is poured into CH2Cl2 (125 mL) and washed with water (2×100 mL). The organic layer is dried (Na2SO4) and the solution filtered. Evaporation of the solvent gives a residue which is purified by column chromatography (methanol/CH2Cl2, 0-6%) to obtain 80 mg of the title compound. Physical characteristics. 1H NMR (400 MHz, DMSO-d6) δ 10.61, 8.71, 7.41-7.20, 4.54, 4.20, 3.96, 3.91, 3.59, 3.41, 3.20, 2.89, 2.82-2.66, 2.40; MS (ESI+) m/z 522 (M+H).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (2×100 mL)
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationthe solution filtered
  5. customEvaporation of the solvent
  6. customgives a residue which
  7. customis purified by column chromatography (methanol/CH2Cl2, 0-6%)

Sources & evidence

ORD record
ord-2cf79acff0724bbea3b299008c63d975
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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