Triethylamine → 1-Chloro-isoquinoline-5-sulfonic acid (2-{[3-(2-benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-ethyl)-amide

HRID 2219216Notes

Reaction equation

HRID 2219216 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.[CH2:16]([C:23]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:24]=1[O:25][CH2:26][CH2:27][CH2:28][N:29]([CH:33]([C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[CH2:30][CH2:31][NH2:32])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC>C(Cl)Cl>[CH2:16]([C:23]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:24]=1[O:25][CH2:26][CH2:27][CH2:28][N:29]([CH:33]([C:42]1[CH:43]=[CH:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=1)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[CH2:30][CH2:31][NH:32][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])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219797811-Chloroisoquinoline-5-sulfonyl chlorideHCID 58816148N1-[3-(2-benzyl-4-chloro-phenoxy)-propyl]-N1-[bis-(4-methoxy-phenyl)-methyl]-ethane-1,2-diamine

Product 1

HCID 866109321-Chloro-isoquinoline-5-sulfonic acid (2-{[3-(2-benzyl-4-chloro-phenoxy)-propyl]-[bis-(4-methoxy-phenyl)-methyl]-amino}-ethyl)-amideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Powdered 1-chloro-isoquinoline-5-sulfonyl chloride (124 mg, 0.473 mmol) is added to a stirred solution of N1-[3-(2-benzyl-4-chloro-phenoxy)-propyl]-N1-[bis-(4-methoxy-phenyl)-methyl]-ethane-1,2-diamine (258 mg, 0.473 mmol) and NEt3 (0.198 mL, 1.42 mmol) in anhydrous CH2Cl2 (5 mL) at ambient temperature under nitrogen. The resultant mixture is allowed to stir for 1 hour. The mixture is chromatographed on silica gel (gradient 0-4% EtOAc in CH2Cl2) to give 285 mg (0.370 mmol, 78% yield) of the title compound as foam. ESIMS: m/z 768 [(M−H)−, 35C, 35Cl], 770 [(M−H)−, 35Cl, 37Cl], 772 [(M−H)−, 37Cl, 37Cl. Analysis for C42H41Cl2N3O5S: calcd: C, 65.45; H, 5.36; N, 5.45; found: C, 65.43; H, 5.27; N, 5.42.

Workup

  1. customThe mixture is chromatographed on silica gel (gradient 0-4% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-a6e91a9fbc3f47079d6fe2286dae9d1d
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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