Tetrahydrofuran → HCID 22719549, compound

HRID 1582145Notes

Reaction equation

HRID 1582145 reaction equation
ClC[C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.[CH2:34]1COCC1>>[CH:18]1([C:17]2[C:11]3[S:10][C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:4]=[CH:3][N:28]=[C:27]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[C:26]=4[CH3:34])=[N:13][C:12]=3[C:14]([O:24][CH3:25])=[CH:15][CH:16]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 22719548HCID 22719548, compound

Product 1

HCID 22719549HCID 22719549, compoundYield 18%

Conditions

Temperature
70 °C

Procedure

To a solution of 0.13 g (0.31 mMol) 2-chloromethyl-N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-isonicotinamide in 1 ml THF were added 0.1 ml (1.3 mMol) pyrrolidine. The reaction mixture was heated to 70° C. for 3 h. The solvent was evaporated to dryness, the residue taken up in dichloro methane and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated to dryness in vacuo. The residue was subjected to column chromatography (dichloro methane/methanol 19:1->9:1) and subsequent crystallization from methanol/ethyl acetate/diethyl ether afforded 0.026 g (18%) of N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-2-pyrrolidin-1-yl-methyl-isonicotinamide as a yellow solid. ES-MS m/e (%): 451 ([M+H]+, 100).

Workup

  1. customThe solvent was evaporated to dryness
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness in vacuo
  5. customThe residue was subjected to column chromatography (dichloro methane/methanol 19:1->9:1) and subsequent crystallization from methanol/ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-3f38d055fffd4b9e8fd6db70ecadff86
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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