4-(2-Aminoethyl)-2,6-dimethoxyphenol → HCID 58603449, compound

HRID 14713Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:14])=[O:13])(C)(C)C.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[C:37]([OH:42])=[C:36]([O:43][CH3:44])[CH:35]=1>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:31][CH2:32][CH2:33][C:34]3[CH:35]=[C:36]([O:43][CH3:44])[C:37]([OH:42])=[C:38]([O:40][CH3:41])[CH:39]=3)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:13])=[O:14]

Participants

Reactant 2

HCID 5339554-(2-Aminoethyl)-2,6-dimethoxyphenol

HCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 58603449HCID 58603449, compound

Procedure

Intermediate 4 was coupled with 4-(2-Amino-ethyl)-2,6-dimethoxy-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 516. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.26 (d, 1H) 8.21 (s, 1H) 8.12 (d, 1H) 7.68 (d, 1H) 7.58 (d, 1H) 7.33 (d, 1H) 6.53 (s, 2H) 4.50 (s, 2H) 3.76 (s, 6H) 3.37 (m, 2H) 2.97 (s, 3H) 2.9 (m, 2H) 2.81 (m, 2H) 1.70 (m, 2H).

Sources & evidence

ORD record: ord-c9fd6ec5fee94a539079e10a1a147fb8
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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