1H-Indol-2-ylboronic acid → HCID 59592996, compound

HRID 2098702Notes

Reaction equation

HRID 2098702 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:6]=2[N:7]=1.[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1B(O)O>>[NH:24]1[C:32]2[C:27](=[C:28]([C:2]3[N:3]=[C:4]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:5]4[S:10][C:9]([CH2:11][N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:6]=4[N:7]=3)[CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25]1

Participants

3

Reactant 2

HCID 225673581H-Indol-2-ylboronic acidHCID 59829400HCID 59829400, compound

Product 1

HCID 59592996HCID 59592996, compound

Procedure

N-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-N-methyl-methanesulfonamide was reacted with indole boronic acid in general procedure A. Purification on silica yielded 194. NMR: (400 MHz, DMSO) 2.83 (s, 3H), 3.02 (s, 3H), 3.85 (t, J=4.7, 4H), 3.99 (t, J=4.7, 4H), 4.64 (s, 2H), 7.19 (t, J=7.7, 1H), 7.43 (m, 2H), 7.51 (m, 2H), 8.12 (d, J=7.3, 1 H), 11.20 (s br, 1H) MS: (ESI+): [M+H]+ 458.01

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-6e9ae4168f27493ca3fde3d92ebe76e1
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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