Methanesulfonyl chloride → HCID 86631908, compound

HRID 1691987Notes

Reaction equation

HRID 1691987 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=4)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:3]1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:24][S:25]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=4)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:3]1)(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66905561HCID 66905561, compound

Product 1

HCID 86631908HCID 86631908, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred, 0° C. solution of (S)-4-(2-(3-hydroxypyrrolidin-1-yl)benzo[d]thiazol-6-yl)benzonitrile (Reference Example 13b, 75 mg, 0.23 mmol) in pyridine (2.5 mL) was treated with methanesulfonyl chloride (0.022 mL, 0.280 mmol). The ice bath was removed and stirring was continued at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give (S)-1-(6-(4-cyanophenyl)benzo[d]thiazol-2-yl)pyrrolidin-3-yl methanesulfonate that was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 2.36-2.50 (m, 1H), 2.53-2.63 (m, 1H), 3.10 (s, 3H), 3.84-4.15 (m, 4H), 5.47-5.52 (m, 1H), 7.60 (dd, J=2, 8 Hz, 1H), 7.67-7.75 (m, 4H), 7.79 (d, J=8 Hz, 1H), 7.85 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 400 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ed78058c50a24cc0b748cd67aa900186
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

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