Dimethylformamide → HCID 58585898, compound

HRID 656338Notes

Reaction equation

HRID 656338 reaction equation
Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)=[O:11])[CH2:5][CH2:4]1.Cl[C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][N:20]=1.C(N(CC)C(C)C)(C)C.CN(C)C=O.C(O)(C(F)(F)F)=O>CO>[OH:2][CH:3]1[CH2:4][CH2:5][CH:6]([NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][N:20]=3)[CH2:13]2)=[O:11])[CH2:7][CH2:8]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 66743585HCID 66743585, compound

Product 1

HCID 58585898HCID 58585898, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (3S)-N-(4-hydroxycyclohexyl)piperidine-3-carboxamide hydrochloride (19.7 mg, 0.0000750 mol, prepared by using a procedure that was analogous to that described for the synthesis of example 1, steps 1 and 2), methyl 6-chloronicotinate (15.4 mg, 0.0000900 mol) and N,N-diisopropylethylamine (37.5 μL, 0.000216 mol) in N,N-dimethylformamide (0.75 mL, 0.0097 mol) was irradiated under microwave at 200° C. for 15 min. The mixture was adjusted with TFA to pH=2.0 and was diluted with methanol (0.8 mL). The resulting solution was purified by prep.-HPLC to give the desired product. LCMS: m/z 362.2 (M+H)+.

Workup

  1. customprepared
  2. customwas irradiated under microwave at 200° C. for 15 min
  3. customThe resulting solution was purified by prep.-HPLC

Sources & evidence

ORD record
ord-1ccf6e3e861f4300902fd4bf8a7302d8
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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