Isonicotinic Acid → HCID 23144751, compound

HRID 1967768Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:13]=[CH:14]C(=O)N(C)[CH:17]=2)=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.[C:20]([OH:28])(=O)[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.C1CN([P+](ON2N=[N:53][C:48]3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH2:62]([N:64]([CH2:67][CH3:68])[CH2:65][CH3:66])C.CN([CH:72]=[O:73])C>O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[N:6]=[C:2]([NH:1][C:20]([C:21]2[CH:22]=[CH:23][N:24]=[C:25]([CH2:62][N:64]3[CH2:67][CH2:68][CH:72]([OH:73])[CH2:66][CH2:65]3)[CH:26]=2)=[O:28])[S:3][C:4]=1[C:12]1[CH:17]=[CH:48][N:53]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Amino-4-(2-furyl)-5-(1-methyl-2-oxo-1,2-dihydropyridin-5-yl)thiazole (200 mg, 0.732 mmol) obtained in Step 1 was dissolved in DMF (4 mL), and isonicotinic acid (180 mg, 1.46 mmol), PyBOP (838 mg, 1.61 mmol) and triethylamine (0.449 mL, 3.21 mmol) were added thereto, followed by stirring at 80° C. for 1 hour. The reaction mixture was poured into water, and the precipitated solid was collected by filtration. The resulting solid was purified through silica gel column chromatography (chloroform:methanol=17:1), followed by reslurrying with methanol to afford the entitled Compound 111 (155 mg, 56%) as a pale yellow solid.

Workup

filtrationthe precipitated solid was collected by filtration
customThe resulting solid was purified through silica gel column chromatography (chloroform:methanol=17:1)

Sources & evidence

ORD record: ord-8cf2a40634484834a64c7ba2ea2910a1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420827B2

Reaction notes

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