Pyridine → HCID 59174884, compound

HRID 1177549Notes

Reaction equation

HRID 1177549 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH2:28])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.N1C=CC=CC=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH:28][S:36]([CH3:35])(=[O:38])=[O:37])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 57397896HCID 57397896, compound

Product 1

HCID 59174884HCID 59174884, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethanamine (100 mg, 0.257 mmol) was dissolved in dichloromethane (2.6 mL) and pyridine (0.208 mL, 2.57 mmol) before methanesulfonyl chloride (30 μl, 0.385 mmol) was added and stirred at ambient temperature for 3 h. The reaction mixture was diluted with 100 mL of DCM, added to a separatory funnel, partitioned with 1 N HCl (aqueous), washed with 1 N HCl (aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give the title compound after purification via preparatory LC. MS (ESI) m/z: Calculated: 467.1; Observed: 468.1 (M++H).

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with 1 N HCl (aqueous)
  3. washwashed with 1 N HCl (aqueous)
  4. customseparated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-ec0fce1d1d254893a62ff760597aa1bd
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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