1-Propyl-1H-pyrazole-3-carboxylic acid → HCID 56847363, compound

HRID 1465182Notes

Reaction equation

HRID 1465182 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[F:23].[CH2:24]([N:27]1[CH:31]=[CH:30][C:29]([C:32](O)=[O:33])=[N:28]1)[CH2:25][CH3:26]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:32]([C:29]2[CH:30]=[CH:31][N:27]([CH2:24][CH2:25][CH3:26])[N:28]=2)=[O:33])=[CH:18][C:17]=1[F:23]

Participants

3

Reactant 2

HCID 64853871-Propyl-1H-pyrazole-3-carboxylic acidHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

Product 1

HCID 56847363HCID 56847363, compoundYield 17%

Procedure

C1 was prepared from A2 and 1-propylpyrazole-3-carboxylic acid following the general procedure reported in Preparative Example 11. The residue was purified by reverse phase RP-HPLC (column: C18), using H2O and ACN as eluents. The desired fractions were lyophilized to yield the title compound C1 (46 mg, 0.10 mmol, 17%) as a white powder. 1H NMR (400 MHz, d6-DMSO, 300K) δ 0.85 (t, J=7.3 Hz, 3H), 1.86 (sext., J=7.3 Hz, 2H), 3.94 (s, 6H), 4.18 (t, J=7.3 Hz, 2H), 6.45 (d, J=5.1 Hz, 1H), 6.79 (d, J=2.3 Hz, 1H), 7.39 (s, 1H), 7.42 (t, J=9.0 Hz, 1H), 7.52 (s, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.90 (d, J=2.3 Hz, 1H), 8.05 (dd, J=13.4 Hz, J=2.3 Hz, 1H), 8.46 (d, J=5.2 Hz, 1H), 10.34 (s, 1H). MS (ES) C24H23FN4O4 requires: 450. Found: 451 (M+H)+.

Workup

  1. customThe residue was purified by reverse phase RP-HPLC (column: C18)

Sources & evidence

ORD record
ord-567023d01889469da051506100abee25
Source dataset
uspto-grants-2015_04
Patent number
US08999982B2

Reaction notes

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