Diisopropylethylamine → HCID 178492302, compound

HRID 1869136Notes

Reaction equation

HRID 1869136 reaction equation
[I:1][C:2]1[C:3]([C:7]([OH:9])=O)=[N:4][NH:5][CH:6]=1.Cl.Cl.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][C:16]=1[NH:21][C:7]([C:3]1[C:2]([I:1])=[CH:6][NH:5][N:4]=1)=[O:9]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 30851614-Methoxybenzene-1,2-diamine dihydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524950HCID 178524950, compound

Product 1

HCID 178492302HCID 178492302, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4-iodo-1H-pyrazole-3-carboxylic acid Compound 1a(500 mg, 2.101 mmol), 4-methoxy-benzene-1,2-diamine dihydrochloride (443 mg, 2.101 mmol), HATU (799 mg, 2.101 mmol), and diisopropyl ethylamine (815 mg, 6.303 mmol) in 15 ml DMF was stirred at 50° C. for 16 hrs. After cooled to rt, the mixture was diluted with 150 ml EtOAc, washed with water (7 times) and brine, then dried with Na2SO4. Evaporation give 4-iodo-1H-pyrazole-3-carboxylic acid (2-amino-5-methoxy-phenyl)-amide Compound 1b (615 mg, 81.7%) as a yellowish powder. NMR (DMSO): δ 3.70 (s, 3H), 6.20 (m, 1H), 6.46 (s, H), 7.12 (d, J=8.0 Hz, 1H), 8.10 (s, 1H). MS m/z 358 (MH+).

Workup

  1. temperatureAfter cooled to rt
  2. washwashed with water (7 times) and brine
  3. dry with materialdried with Na2SO4
  4. customEvaporation

Sources & evidence

ORD record
ord-73879678139e41ff9a3d256da643ba4f
Source dataset
uspto-grants-2009_12
Patent number
US07638518B2

Reaction notes

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