Triethylamine → [2-(1-Chloro-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

HRID 2219202Notes

Reaction equation

HRID 2219202 reaction equation
[Cl:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH2:25])([CH3:19])([CH3:18])[CH3:17].CCN(CC)CC>C(Cl)Cl>[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH:25][S:12]([C:7]1[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:14])=[O:13])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 219797811-Chloroisoquinoline-5-sulfonyl chloride

Product 1

HCID 21979959[2-(1-Chloro-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Powdered 1-chloro-isoquinoline-5-sulfonyl chloride (10.0 g, 38.2 mmol) is added in portions to a stirred solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (7.33 g, 45.8 mmol) and NEt3 (10.7 mL, 76.4 mmol) in anhydrous CH2Cl2 (200 mL) at 0° C. under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 4 hours. The mixture is concentrated and chromatographed on silica gel (gradient 0-5% CH3OH in CH2Cl2) to give 13.8 g (35.8 mmol, 94% yield) of the title compound as foam. ESIMS: m/z 386 [(M+H)+, 35Cl], 388 [(M+H)+, 37Cl]. Analysis for C16H20ClN3O4S: calcd: C, 49.80; H, 5.22; N, 10.89; found: C, 49.70; H, 5.22; N, 10.72.

Workup

  1. concentrationThe mixture is concentrated
  2. customchromatographed on silica gel (gradient 0-5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-ddcaa62558d64432ba880d8f0a2750a8
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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