1,2-Dichloroethane → HCID 52932049, compound

HRID 877352Notes

Reaction equation

HRID 877352 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[Cl-].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]([C:24]2[N:25]=[N:26][N:27]([CH3:29])[CH:28]=2)[NH3+:23])=[CH:18][CH:17]=1.C(Cl)CCl.C(N(CC)CC)C>CN(C=O)C>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]([C:24]2[N:25]=[N:26][N:27]([CH3:29])[CH:28]=2)[NH:23][C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([CH:1]3[CH2:2][CH2:3]3)=[CH:9][CH:8]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 204905282-(4-Cyclopropylphenyl)acetic acidHCID 86668958HCID 86668958, compound

Product 1

HCID 52932049HCID 52932049, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.075 g (0.426 mmol) (4-cyclopropylphenyl)acetic acid in 0.850 ml DMF was added 0.194 g (0.638 mmol) (S)-(4-bromophenyl)(1-methyl-1H-1,2,3-triazol-4-yl)methanaminium chloride 0.063 g (0.468 mmol) HOAT, 0.090 g (0.468 mmol) EDC, and 0.186 mL (1.06 mmol) triethylamine. After 24 hr at room temperature, the reaction mixture was purified by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) to afford 0.160 g (88%) N-[(S)-(4-bromophenyl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-cyclopropylphenyl)acetamide. 1H NMR (CDCl3, 400 MHz) 7.43-7.40 (m, 2H); 7.39 (m, 1H); 7.14 (m, 4H); 7.03 (d, 2H, J=8.25 Hz); 6.73 (d, 1H, J=7.41 Hz); 6.20 (d, 1H, J=7.50 Hz); 4.04 (s, 3H); 3.56 (s, 2H); 1.91-1.84 (m, 1H); 0.98-0.94 (m, 2H); 0.70-0.66 (m, 2H). HRMS (ES) [M+1]+ calcd for C21H21BrN4O: 425.0977. Found: 425.0979.

Workup

  1. customthe reaction mixture was purified by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18)

Sources & evidence

ORD record
ord-8f9eabd73c4f47128a95225d8e3a749d
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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