Pyridine → [2-(7-Bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

HRID 2219198Notes

Reaction equation

HRID 2219198 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:12](Cl)(=[O:14])=[O:13])[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:11]=1.[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH2:25])([CH3:19])([CH3:18])[CH3:17].N1C=CC=CC=1>C(Cl)Cl>[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH:25][S:12]([C:4]1[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:11]=[C:2]([Br:1])[CH:3]=1)(=[O:14])=[O:13])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 187201N-BOC-ethylenediamineHCID 588161467-Bromoisoquinoline-5-sulfonyl chloride

Product 1

HCID 58816140[2-(7-Bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A slurry of 7-bromo-isoquinoline-5-sulfonyl chloride (16.3 g, 35.5 mmol) in CH2Cl2 (200 mL) is added in small portions to a stirred solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (6 mL, 37.9 mmol) and pyridine (2.79 mL, 34.5 mmol) in CH2Cl2 (100 mL) at 0° C. under nitrogen. The resultant mixture is allowed to stir at ambient temperature overnight. The mixture is diluted with another 100 mL CH2Cl2, washed with saturated aqueous NaHCO3 (150 mL) solution, dried, filtered and concentrated. The dark oil is subject to column chromatography (Biotage 75 short; eluted with 10-20% CH3CN/CH2Cl2+0.2% NEt3) to give the title compound as a white solid. ESIMS: m/z 430 [(M+H)+, 79Br], 432 [(M+H)+, 81Br].

Workup

  1. washwashed with saturated aqueous NaHCO3 (150 mL) solution
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe dark oil is subject to column chromatography (Biotage 75 short; eluted with 10-20% CH3CN/CH2Cl2+0.2% NEt3)

Sources & evidence

ORD record
ord-b389aa74b15448c4923b40c7644e820e
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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