Diisopropylethylamine → HCID 66906080, compound

HRID 2040967Notes

Reaction equation

HRID 2040967 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][C@@H:29]1[CH2:33][CH2:32][CH2:31][NH:30]1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:28][C@@H:29]1[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:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=4)[CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 641544(R)-2-MethylpyrrolidineHCID 86631908HCID 86631908, compound

Product 1

HCID 66906080HCID 66906080, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of (S)-1-(6-(4-cyanophenyl)benzo[d]thiazol-2-yl)pyrrolidin-3-yl methanesulfonate (Reference Example 13c, 32 mg, 0.080 mmol), (R)-2-methylpyrrolidine (27.3 mg, 0.320 mmol), and N,N-diisopropylethylamine (0.17 mL, 0.961 mmol) in acetonitrile (2 mL) was heated to 150° C. under microwave irradiation for 20 minutes. The reaction mixture was cooled to room temperature then purified by silica gel chromatography (98:2:0 to 98:2:1 dichloromethane/methanol/aqueous NH4OH). Fractions containing product were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give to give 4-(2-((2R,3′R)-2-methyl-1,3′-bipyrrolidin-1′-yl)benzo[d]thiazol-6-yl)benzonitrile. 1H NMR (300 MHz, CD3OD) δ ppm 1.17 (d, J=6 Hz, 3H), 1.45-1.57 (m, 1H), 1.73-1.90 (m, 2H), 1.98-2.20 (m, 2H), 2.24-2.35 (m, 1H), 2.62 (q, J=8 Hz, 1H), 2.83-2.96 (m, 1H), 2.99-3.08 (m, 1H), 3.36-3.62 (m, 3H), 3.69-3.78 (m, 1H), 3.86-3.93 (m, 1H), 7.57 (d, J=8 Hz, 1H), 7.65 (dd, J=2, 9 Hz, 1H), 7.80 (q, J=9 Hz, 4H), 8.03 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 389 (M+H)+.

Workup

  1. customthen purified by silica gel chromatography (98:2:0 to 98:2:1 dichloromethane/methanol/aqueous NH4OH)
  2. additionFractions containing product
  3. dry with materialwere dried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-0bfa020c9f664b248717686bd93b333c
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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