1-Hydroxybenzotriazole → 1-(1-{2-[Cis-2,5-dipropylpyrrolidin-1-yl]-2-oxoethyl}-6-methoxy-1H-indazol-3-yl)-2,2-dimethylpropan-1-one

HRID 490805Notes

Reaction equation

HRID 490805 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]([C@H:35]1[CH2:39][CH2:38][C@@H:37]([CH2:40][CH2:41][CH3:42])[NH:36]1)[CH2:33][CH3:34].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH2:32]([C@H:35]1[CH2:39][CH2:38][C@@H:37]([CH2:40][CH2:41][CH3:42])[N:36]1[C:17](=[O:19])[CH2:16][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:5]([C:3](=[O:4])[C:2]([CH3:21])([CH3:1])[CH3:20])=[N:6]1)[CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 14564783(2R,5S)-2,5-DipropylpyrrolidineHCID 57675531[3-(2,2-Dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid

Product 1

HCID 100255631-(1-{2-[Cis-2,5-dipropylpyrrolidin-1-yl]-2-oxoethyl}-6-methoxy-1H-indazol-3-yl)-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 28.3 mg [3-(2,2-dimethylpropanoyl)-6-methoxy-1H-indazol-1-yl]acetic acid from the Step E Example 44 in 1 mL DMF was added 23.0 mg HOBt, 23.3 mg cis-2,5-dipropylpyrrolidine from the Step A above, 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 70-100% MeCN gradient. The pure product fractions were pooled and lyophilized to give the title compound as white solid. LC-MS: 4.50 min. (m/Z=428.4, 450.3).

Workup

  1. custompurified by RP-HPLC using 70-100% MeCN gradient

Sources & evidence

ORD record
ord-8ed9d08e89054625850d67c05e7e660f
Source dataset
uspto-grants-2009_05
Patent number
US07528163B2

Reaction notes

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