1H-Indol-2-ylboronic acid → HCID 59593001, compound

HRID 2098693

Reaction equation

HRID 2098693 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:16][C:15]2[C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:13][C:12]([CH3:23])=[N:11][C:10]=2[CH:9]=1)=[O:7].[NH:24]1[C:32]2[C:27](=C[CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1B(O)O>>[NH:24]1[C:32]2[C:27](=[C:23]([C:12]3[N:13]=[C:14]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:15]4[S:16][C:8]([C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7])=[CH:9][C:10]=4[N:11]=3)[CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25]1

Participants

3

Reactant 2

HCID 225673581H-Indol-2-ylboronic acidHCID 67190260HCID 67190260, compound

Product 1

HCID 59593001HCID 59593001, compound

Procedure

2-Methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxylic acid (2-methoxyethyl)-amide was reacted with indole boronic acid in general procedure A. Purification on silica yielded 189. NMR: 400MHz; CDCl3 3.44 (3H, s); 3.60 (2H, m); 3.70 (2H, m); 3.92 (4H, t, J=4.8 Hz); 4.15 (4H,t,J=4.8Hz); 6.74 (1H,br t); 7.30 (1H,d,J=7.8Hz); 7.35 (1H,m); 7.52 (1H,d,J=8.0Hz); 7.57 (1H,s); 7.82 (1H,s); 8.2 0(1H,d,J=7.4Hz); 8.30 (1H,br s). MS: (ESI+) M+H (438)

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-a4d6cb2db0164f5080eeb6f2d9ee173a
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Linked notes

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