5-(2-hydroxyethoxy)-1H-indole-2-carboxylic acid → HCID 11497597, compound

HRID 2238374Notes

Reaction equation

HRID 2238374 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:9]=3[C:8]([N+:20]([O-:22])=[O:21])=[CH:7][C:6]=2[NH:5][CH2:4]1.[OH:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31]([C:36](O)=[O:37])=[CH:30]2>>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:9]=3[C:8]([N+:20]([O-:22])=[O:21])=[CH:7][C:6]=2[N:5]([C:36]([C:31]2[NH:32][C:33]3[C:29]([CH:30]=2)=[CH:28][C:27]([O:26][CH2:25][CH2:24][OH:23])=[CH:35][CH:34]=3)=[O:37])[CH2:4]1

Participants

3

Reactant 2

HCID 184556225-(2-hydroxyethoxy)-1H-indole-2-carboxylic acidHCID 445494021-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

Product 1

HCID 11497597HCID 11497597, compoundYield 88%

Procedure

(Scheme C). The amine 117 was reacted with 5-(2-hydroxyethoxy)-1H-indole-2-carboxylic acid as described in Example 7. The reaction mixture was poured into ice-water and the precipitate was collected to give 28 (88%): mp (EtOAc) 231-234° C.; 1H NMR [(CD3)2SO] δ 11.72 (s, 1H), 9.28 (s, 1H), 8.87 (d, J=1.6 Hz, 1H), 8.44 (d, J=8.9 Hz, 1H), 7.97 (dd, J=8.9, 1.6 Hz, 1H), 7.63 (s, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.22 (d, J=1.7 z, 1H), 7.17 (d, J=2.2 Hz, 1H), 6.97 (dd, J=8.9, 2.4 Hz, 1H), 5.00-4.93 (m, 1H), 4.188-4.81 (m, 1H), 4.74-4.70 (m, 1H), 4.69-4.60 (m, 1H), 4.19-4.12 (m, 2H), 4.05-3.98 (m, 2H), 3.79-3.71 (m, 2H), 2.94 (s, 1H), 2.79 (s, 1H), 1.95 (s, 1H); 13C NMR δ 160.6, 153.2, 147.0, 142.6, 142.5, 132.2, 131.9, 130.4, 129.7, 127.4, 125.6, 124.4, 121.3, 120.5, 116.5, 116.1, 113.2, 106.3, 103.1, 69.8, 59.6, 54.8, 47.6, 41.4. Anal. (C24H21ClN4O7S.⅓H2O) C, H, N.

Workup

  1. customthe precipitate was collected

Sources & evidence

ORD record
ord-71058e74ff0f42b6bd90459f257949bd
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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