1,2-Dichloroethane → tert-butyl 2-(4-(5-(2-amino-5-methoxyphenylcarbamoyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)piperidin-1-yl)ethyl(methyl)carbamate

HRID 2196548Notes

Reaction equation

HRID 2196548 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:29])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]([C:22](O)=[O:23])=[CH:20][C:19]([C:25]([F:28])([F:27])[F:26])=[N:18]2)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[CH3:46][O:47][C:48]1[CH:53]=[CH:52][C:51]([NH2:54])=[C:50]([NH2:55])[CH:49]=1>CN(C=O)C>[NH2:54][C:51]1[CH:52]=[CH:53][C:48]([O:47][CH3:46])=[CH:49][C:50]=1[NH:55][C:22]([C:21]1[N:17]([CH:14]2[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][N:8]([CH3:29])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:12][CH2:13]2)[N:18]=[C:19]([C:25]([F:27])([F:28])[F:26])[CH:20]=1)=[O:23]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 30851614-Methoxybenzene-1,2-diamine dihydrochlorideHCID 598432141-(1-(2-(tert-butoxycarbonyl(methyl)amino)ethyl)piperidin-4-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 59843143tert-butyl 2-(4-(5-(2-amino-5-methoxyphenylcarbamoyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)piperidin-1-yl)ethyl(methyl)carbamateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 96 (160 mg, 0.381 mmol) in DMF (1.903 mL) was added EDC (88 mg, 0.457 mmol), HOBT (69.9 mg, 0.457 mmol) followed by 4-Methoxy-o-phenylenediamine dihydrochloride (73.1 mg, 0.419 mmol). The mixture was stirred for 16 h at room temperature. After the usual work-up, the residue was purified via Biotage (5% to 15% MeOH/CH2Cl2; 12M column) to afford 106 (172 mg, 84% yield) as yellow oil. LRMS (ESI): calc. 540.6; found 541.4 (MH)+.

Workup

  1. customAfter the usual work-up, the residue was purified via Biotage (5% to 15% MeOH/CH2Cl2; 12M column)

Sources & evidence

ORD record
ord-6882ce41f0ae4569921c4bafbdc096b7
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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