Dimethylformamide → HCID 66906056, compound

HRID 1691996Notes

Reaction equation

HRID 1691996 reaction equation
CS(O[C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=4)[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:7]1)(=O)=O.[CH3:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][NH:30]1.CN(C)C=O>C(O)(C)C>[CH3:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][N:30]1[C@H:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=4)[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 79742-MethylpiperidineHCID 86631909HCID 86631909, compound

Product 1

HCID 66906056HCID 66906056, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of (R)-1-(6-(4-cyanophenyl)benzo[d]thiazol-2-yl)pyrrolidin-3-yl methanesulfonate (Reference Example 14b, 20 mg, 0.050 mmol), 2-methylpiperidine (0.029 mL, 0.25 mmol), and N,N-dimethylformamide (0.01 mL) in isopropanol (0.50 mL) was heated at 150° C. under microwave irradiation for 15 minutes. The reaction mixture was cooled to room temperature, concentrated, and purified by silica gel chromatography (100:0 to 70:30 dichloromethane/ethyl acetate, then 98:2 to 92:8 dichloromethane/methanol). Fractions containing product were combined and concentrated under reduced pressure to give 4-(2-((3S)-3-(2-methylpiperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazol-6-yl)benzonitrile. 1H NMR (300 MHz, CD2Cl2) δ ppm 1.06-1.12 (m, 3H), 1.37-1.45 (m, 2H), 1.54-1.61 (m, 1H), 1.67-1.77 (m, 2H), 2.01-2.16 (m, 2H), 2.19-2.29 (m, 1H), 2.35-2.51 (m, 1H), 2.63-2.70 (m, 1H), 2.81-2.95 (m, 1H), 3.36-3.50 (m, 1H), 3.50-3.79 (m, 5H), 7.55 (s, 2H), 7.72 (s, 4H), 7.88 (s, 1H); MS (ESI) m/z 403 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel chromatography (100:0 to 70:30 dichloromethane/ethyl acetate
  3. additionFractions containing product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84a4b9d984564a449a5e242551f7386d
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

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