Isopropyl iodide → 4'-Fluoro-biphenyl-4-carboxylic Acid {2-[(1-isopropyl-pyrrolidin-3-ylmethyl)-methyl-amino]-benzothiazol-6-yl}-amide

HRID 1174958Notes

Reaction equation

HRID 1174958 reaction equation
[CH3:1][N:2]([CH2:28][CH:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)[C:3]1[S:4][C:5]2[CH:11]=[C:10]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[CH:17][CH:16]=3)=[O:14])[CH:9]=[CH:8][C:6]=2[N:7]=1.I[CH:35]([CH3:37])[CH3:36].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH:35]([N:31]1[CH2:32][CH2:33][CH:29]([CH2:28][N:2]([CH3:1])[C:3]2[S:4][C:5]3[CH:11]=[C:10]([NH:12][C:13]([C:15]4[CH:16]=[CH:17][C:18]([C:21]5[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=5)=[CH:19][CH:20]=4)=[O:14])[CH:9]=[CH:8][C:6]=3[N:7]=2)[CH2:30]1)([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 577717144'-Fluoro-biphenyl-4-carboxylic acid [2-(methyl-pyrrolidin-3-ylmethyl-amino)-benzothiazol-6-yl]-amide

Product 1

HCID 115478714'-Fluoro-biphenyl-4-carboxylic Acid {2-[(1-isopropyl-pyrrolidin-3-ylmethyl)-methyl-amino]-benzothiazol-6-yl}-amideYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Place 4′-fluoro-biphenyl-4-carboxylic acid [2-(methyl-pyrrolidin-3-ylmethyl-amino)-benzothiazol-6-yl]-amide (16 mg, 0.035 mmol), 2-iodopropane (0.007 mL, 0.070 mmol), and potassium carbonate (15 mg, 0.108 mmol) in DMF (2 mL) and stir at rt for 3 d. Dilute the reaction with ethyl acetate and wash the organic layer with water (5 times). Chromatograph (silica gel, eluting with 10% 2M NH3 in MeOH:DCM) to yield 16 mg (91%) of the title compound: mass spectrum (ion-spray): (m/z)=503.3 (M+1).

Workup

  1. additionDilute
  2. washwash the organic layer with water (5 times)
  3. washChromatograph (silica gel, eluting with 10% 2M NH3 in MeOH:DCM)

Sources & evidence

ORD record
ord-22c08cf3e6c3423583f32028e377de7c
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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