1-Hydroxybenzotriazole → 1-(6-methoxy-1-{2-[trans-octahydroisoquinolin-2 (1H)-yl]-2-oxoethyl}-1H-indazol-3-yl)-2,2-dimethylpropan-1-one

HRID 490798Notes

Reaction equation

HRID 490798 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[N:7]([CH2:16][C:17]([OH:19])=O)[N:6]=1)=[O:4].C1C=CC2N(O)N=NC=2C=1.[CH2:32]1[C@H:41]2[C@@H:36]([CH2:37][CH2:38][CH2:39][CH2:40]2)[CH2:35][CH2:34][NH:33]1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH3:15][O:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([C:3](=[O:4])[C:2]([CH3:21])([CH3:1])[CH3:20])=[N:6][N:7]2[CH2:16][C:17]([N:33]2[CH2:34][CH2:35][C@H:36]3[C@@H:41]([CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:32]2)=[O:19])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11083964trans-DecahydroisoquinolineHCID 57675531[3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid

Product 1

HCID 103869371-(6-methoxy-1-{2-[trans-octahydroisoquinolin-2 (1H)-yl]-2-oxoethyl}-1H-indazol-3-yl)-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 29.0 mg [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid in 1 mL DMF was added 23.0 mg HOBt, 20.9 mg trans-decahydroisoquinoline, 38.3 mg EDC, and 45.2 mg DIEA in that order. The mixture was stirred at room temperature over night and purified by RP-HPLC using 65-100% MeCN gradient. The pure product fractions were pooled and lyophilized to give the title compound. LC-MS: 4.29 min. (m/Z=412.3, 434.3).

Workup

  1. custompurified by RP-HPLC using 65-100% MeCN gradient

Sources & evidence

ORD record
ord-bd375311500a4842a5d0d62c0fd11f70
Source dataset
uspto-grants-2009_05
Patent number
US07528163B2

Reaction notes

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