Dichloromethane → N-(3-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-hydroxyphenyl)-5-methylisoxazole-3-carboxamide

HRID 1425538Notes

Reaction equation

HRID 1425538 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C:44]1[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([C:51]2[N:55]([CH3:56])[N:54]=[CH:53][CH:52]=2)[CH:45]=1.C(Cl)[Cl:58]>>[Cl:58][C:52]1[CH:53]=[N:54][N:55]([CH3:56])[C:51]=1[C:46]1[CH:45]=[C:44]([NH:43][C:7]([C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)=[O:9])[CH:49]=[CH:48][C:47]=1[OH:50]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1355820244-amino-2-(1-methyl-1H-pyrazol-5-yl)phenol

Product 1

HCID 136388020N-(3-(4-chloro-1-methyl-1H-pyrazol-5-yl)-4-hydroxyphenyl)-5-methylisoxazole-3-carboxamideYield 59%

Procedure

To a solution of 5-methylisoxazole-3-carboxylic acid (284.0 mg, 2236.0 μmol) dissolved in DCM(10.0 mL) was added HATU (1020.0 mg, 2683.0 μmol) followed by DIEA (586 μl, 3353 μmol). The solution was stirred at room temperature for 5 minutes. 4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenol (500.00 mg, 2236 μmol) was added and the reaction mixture was stirred at 25° C. for 15 hours. The reaction mixture was subjected to purification by column chromatography (ethyl acetate:hexane 50:50) to afford the title compound as an off-white solid in 59.0% yield. LCMS m/z=333.2 (M+H), 1H NMR (400 MHz, DMSO-d6) δ ppm 2.69 (s, 3 H), 3.66 (s, 3 H), 6.64 (s, 1 H), 7.00 (d, J=8.84 Hz, 1 H), 7.61 (s, 1 H), 7.64 (d, J=2.53 Hz, 1 H), 7.73 (dd, J=8.84, 2.53 Hz, 1 H), 10.04 (s, 1 H), 10.60 (s, 1 H).

Workup

  1. stirringthe reaction mixture was stirred at 25° C. for 15 hours
  2. customThe reaction mixture was subjected to purification by column chromatography (ethyl acetate:hexane 50:50)

Sources & evidence

ORD record
ord-4be2405866b24d04a2c08a8ea89f26ca
Source dataset
uspto-grants-2015_01
Patent number
USRE045336E1

Reaction notes

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