Diisopropylamine → 4-(2-{6-[4-(2-Isopropylaminoethylamino)benzenesulfonyloxy]-benzothiazol-2-ylcarbamoyl}ethyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1867969Notes

Reaction equation

HRID 1867969 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22][S:23]([C:26]4[CH:31]=[CH:30][C:29]([NH:32][CH2:33][CH2:34][NH:35][CH:36]([CH3:38])[CH3:37])=[CH:28][CH:27]=4)(=[O:25])=[O:24])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[O:11])[CH2:4][CH2:3]1.[C:39]([O:43][C:44](N1CCC(CCC(=O)NC2SC3C=C(OS(C4C=CC(F)=CC=4)(=O)=O)C=CC=3N=2)CC1)=[O:45])([CH3:42])([CH3:41])[CH3:40].C(NC(C)C)(C)C>>[C:39]([O:43][C:44]([N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][C:10](=[O:11])[NH:12][C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22][S:23]([C:26]4[CH:27]=[CH:28][C:29]([NH:32][CH2:33][CH2:34][NH:35][CH:36]([CH3:38])[CH3:37])=[CH:30][CH:31]=4)(=[O:24])=[O:25])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:4][CH2:3]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]

Participants

4

Reactant 3

HCID 7912DiisopropylamineHCID 116786974-(2-Isopropylaminoethylamino)-benzenesulfonic acid 2-(3-piperid-4-ylpropionylamino)benzothiazol-6-yl ester hydrochlorideHCID 579808644-{2-[6-(4-Fluorobenzenesulfonyloxy)-benzothiazol-2-ylcarbamoyl]ethyl}piperidine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 866121484-(2-{6-[4-(2-Isopropylaminoethylamino)benzenesulfonyloxy]-benzothiazol-2-ylcarbamoyl}ethyl)piperidine-1-carboxylic acid tert-butyl ester

Procedure

According to the method of example 18, 4-(2-isopropylaminoethylamino)-benzenesulfonic acid 2-(3-piperid-4-ylpropionylamino)benzothiazol-6-yl ester hydrochloride is prepared by combining 4-{2-[6-(4-fluorobenzenesulfonyloxy)-benzothiazol-2-ylcarbamoyl]ethyl}piperidine-1-carboxylic acid tert-butyl ester (intermediate 23) with N,N-diisopropylamine. The compound obtained from the first step (4-(2-{6-[4-(2-isopropylaminoethylamino)benzenesulfonyloxy]-benzothiazol-2-ylcarbamoyl}ethyl)piperidine-1-carboxylic acid tert-butyl ester) is purified on a flash cartridge of 5 g of silica of porosity 15-35μ, with a gradient of from 1% to 10% of methanol in dichloromethane.

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-582c2639ff43465f9cafaf8ed59db8e2
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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