4-(5-Hydroxypent-1-yn-1-yl)benzoic acid → N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-hydroxypent-1-yn-1-yl)benzamide

HRID 385265Notes

Reaction equation

HRID 385265 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:33][CH3:34])=[C:10]([CH2:19][NH:20][C:21](=[O:32])[C:22]3[CH:27]=[CH:26][CH:25]=[C:24](CC(=O)C)[CH:23]=3)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[OH:35][CH2:36][CH2:37][CH2:38][C:39]#[C:40]C1C=CC(C(O)=O)=CC=1>>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:33][CH3:34])=[C:10]([CH2:19][NH:20][C:21](=[O:32])[C:22]3[CH:23]=[CH:24][C:25]([C:40]#[C:39][CH2:38][CH2:37][CH2:36][OH:35])=[CH:26][CH:27]=3)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 575175834-(5-Hydroxypent-1-yn-1-yl)benzoic acidHCID 58505292N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-3-(2-oxopropyl)benzamide

Product 1

HCID 58505289N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-hydroxypent-1-yn-1-yl)benzamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 29, using Intermediate 21 in place of 3-(2-oxopropyl)benzoic acid. ES/MS calcd. for C28H36N5O3+ 490.3. found m/z=490.4 (M+H)+.

Sources & evidence

ORD record
ord-6ea66787979c441daea28eb25f992d6f
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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