Diisopropylethylamine → 3-Benzyloxy-5-isopropoxy-N-(5-methyl-1-pyridine-2-ylmethyl-1H-pyrazole-3-yl)-benzamide

HRID 883046Notes

Reaction equation

HRID 883046 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:51][C:52]1[N:56]([CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=2)[N:55]=[C:54]([NH2:64])[CH:53]=1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:17]=1)[C:12]([NH:64][C:54]1[CH:53]=[C:52]([CH3:51])[N:56]([CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=2)[N:55]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 124335Benzotriazol-1-yloxy-tris(dimethylamino)phosphoniumHCID 534011033-Benzyloxy-5-isopropoxybenzoic acidHCID 674861155-methyl-1-pyridine-2-ylmethyl-1H-pyrazole-3-ylamine

Product 1

HCID 252616693-Benzyloxy-5-isopropoxy-N-(5-methyl-1-pyridine-2-ylmethyl-1H-pyrazole-3-yl)-benzamideYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Benzyloxy-5-isopropoxy-benzoic acid (0.35 mmol) is dissolved in acetonitrile, di-isopropyl ethyl amine (3 eq.), benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium (1.2 eq.) and 5-methyl-1-pyridine-2-ylmethyl-1H-pyrazole-3-ylamine (1.0 eq., prepared similar to 1-pyridine-2-ylmethyl-1H-pyrazole-3-ylamine) is added and stirred at RT for 14 hours. The solvent is removed in vacuo. 3-Benzyloxy-5-isopropoxy-N-(5-methyl-1-pyridine-2-ylmethyl-1H-pyrazole-3-yl)-benzamide is obtained after column chromatography (chloroform (methanol) as a colourless powder in a yield of 31%; HPLC (Method B): 3.25 min; LC-MS: 2.350 min, 457.15 (M÷H+);

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-068df13f3744401ca881141b395f2579
Source dataset
uspto-grants-2012_08
Patent number
US08236824B2

Reaction notes

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