Diethylamine → HCID 11604907, compound

HRID 2240154Notes

Reaction equation

HRID 2240154 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15]4[N:19]([C:20]5[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=5)[N:18]=[CH:17][CH:16]=4)[CH:13]=3)[C:8]([CH2:29][CH3:30])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:31]([NH:33][CH2:34][CH3:35])[CH3:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15]4[N:19]([C:20]5[CH:21]=[CH:22][C:23]([C:24]([N:33]([CH2:34][CH3:35])[CH2:31][CH3:32])=[O:26])=[CH:27][CH:28]=5)[N:18]=[CH:17][CH:16]=4)[CH:13]=3)[C:8]([CH2:29][CH3:30])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11524159HCID 11524159, compound

Product 1

HCID 11604907HCID 11604907, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 1-neck round-bottom flask was added 4-[5-(1-cyclopentyl-3-ethyl-1H-indazol-6-yl)-1H-pyrazol-1-yl]benzoic acid (50.0 mg, 0.125 mmol), 2 mL of N,N-dimethylformamide, diethylamine (0.00913 g, 0.125 mmol), HATU (47.4 mg, 0.125 mmol) and N,N-diisopropylethylamine (43.5 uL, 0.250 mmol). The reaction was stirred for 3 days at room temperature, concentrated under reduced pressure, and purified by preparative HPLC (UV detection) to give 33 mg (0.0725 mmol, 58%) of 4-[5-(1-cyclopentyl-3-ethyl-1H-indazol-6-yl)-1H-pyrazol-1-yl]-N,N-diethylbenzamide as a clear oil. LC/MS (EI) tR 5.26 (Method C), m/z 456.1 (M++1). 1H NMR (CDCl3 300 MHz) δ 1.0-1.2 (m, 5H); 1.3 (t, 3H); 1.7-1.9 (m, 5H); 2.0 (m, 4H); 3.0 (q, 2H); 3.1 (br s, 2H); 3.4 (br s, 2H); 4.8 (m, 1H); 6.6 (s, 1H); 6.9 (d, 1H); 7.2 (m, 5H); 7.5 (d, 1H); 7.7 (s, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by preparative HPLC (UV detection)

Sources & evidence

ORD record
ord-b4d0f0ea7fb74643a5f2beeec4743274
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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