Diisopropylethylamine → HCID 69314204, compound

HRID 2055654Notes

Reaction equation

HRID 2055654 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[N:6][CH:5]=1.C(N(C(C)C)CC)(C)C.[CH2:21]([O:28][C:29](=[O:38])[NH:30][CH:31]([C:35](F)=[O:36])[CH:32]([CH3:34])[CH3:33])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:9]([NH:10][C:35](=[O:36])[CH:31]([NH:30][C:29]([O:28][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:38])[CH:32]([CH3:34])[CH3:33])=[CH:8][CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 592353Methyl 4-aminopyridine-3-carboxylateHCID 14824297HCID 14824297, compound

Product 1

HCID 69314204HCID 69314204, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formula 506 where R1, R3 and R4 are H; R6 is Isopropyl; R6′ is H: W, Y and Z are —C═; and X is —N═: To a solution of dichloromethane (100 mL), 4-amino-nicotinic acid methyl ester (4.60 g, 30.2 mmol) and diisopropylethyl amine (8.25 mL, 46.7 mmol), was added (1-fluorocarbonyl-2-methyl-propyl)-carbamic acid benzyl ester (11.8 g, 46.7 mmol) at room temperature and the mixture stirred overnight. The solvent was removed under reduced pressure and the residue purified by flash silica gel chromatography using hexane-EtOAc (stepwise gradient from 3:1 to 1:1) as eluents to obtain the desired amide of Formula 506, 4-(2-benzyloxycarbonylamino-3-methyl-butyrylamino)-nicotinic acid methyl ester (10.5 g, 90.1%). MS (Cl) M/E: 386.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-b859c654f8ef40038851f79faaa448fe
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

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