Methanol → HCID 131726995, compound

HRID 2219236Notes

Reaction equation

HRID 2219236 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1)(=[O:7])=[O:6].Br[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C.C(Cl)(Cl)Cl.O>[ClH:28].[ClH:28].[C:29]([C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][NH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][C:14]=2[CH:15]=[CH:16][CH:17]=1)(=[O:7])=[O:6])(=[O:30])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 3544N-(2-Aminoethyl)isoquinoline-5-sulfonamideHCID 11430Potassium CarbonateHCID 69275104HCID 69275104, compound

Product 1

HCID 131726995HCID 131726995, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide (20 mg, 0.080 mmol), [2-(2-bromo-ethoxy)-5-chloro-phenyl]-phenyl-methanone (29 mg (0.085 mmol) and potassium carbonate (18 mg, 0.13 mmol) in anhydrous DMF (0.12 mL) is stirred at ambient temperature for 14 hours. After dilution with 10% MeOH in CHCl3, the mixture is poured into 10 mL of water and extracted three times with 10% MeOH in CHCl3. The extracts are dried over Na2SO4 and evaporated. The crude residue is purified by column chromatography to afford 27 mg (66%) of the free amine product. APCI-MS: m/z 510 [(M+H)+, 35Cl], 512 [(M+H)+, 37Cl]. APCI-MS: [M−H]−: m/z 508, 510. 1H-NMR (300 MHz; CDCl3): δ9.34 (1H, s); 8.63 (1H, d, 6.2 Hz); 8.42 (2H, t, 7.0 Hz); 8.20 (1H, d, 8.1 Hz); 7.73 (2H, d, 7.8 Hz); 7.67-7.75 (3H, m); 7.36-7.51 (5H,m); 6.85 (1H, d, 8.6 Hz); 3.80 (2H, t, 4.6 Hz); 2.82 (2H, t, 5.5 Hz); 2.40 (2H, t, 4.6 Hz); 2.35 (2H, t, 5.5 Hz).

Workup

  1. extractionextracted three times with 10% MeOH in CHCl3
  2. dry with materialThe extracts are dried over Na2SO4
  3. customevaporated
  4. customThe crude residue is purified by column chromatography

Sources & evidence

ORD record
ord-96ac628350114f83965db36a287b80f4
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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