1,2-Dichloroethane → HCID 71281144, compound

HRID 475957Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:22][CH2:23][C:24]1[C:25](=[O:34])[NH:26][C:27]([CH2:31][CH2:32][CH3:33])=[CH:28][C:29]=1[CH3:30].C(O)(C(F)(F)F)=O.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)[CH:11]=[C:12]([C:13]([NH:22][CH2:23][C:24]3[C:25](=[O:34])[NH:26][C:27]([CH2:31][CH2:32][CH3:33])=[CH:28][C:29]=3[CH3:30])=[O:15])[C:7]=2[CH:6]=[N:5]1)[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

1-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (192 mg, 0.680 mmol), 3-(aminomethyl)-4-methyl-6-propyl-2(1H)-pyridinone.TFA (200 mg, 0.680 mmol), HOAT (139 mg, 1.019 mmol), EDC (195 mg, 1.019 mmol), and N-methylmorpholine (0.299 mL, 2.72 mmol) were sequentially added to DMF (6 mL), and the mixture stirred at 40° C. overnight. The reaction mixture was then filtered. The collected solid was washed with ethanol, and dried, affording the final product as a white solid, 0.160 g (53%). LCMS E-S (M+H)=445.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.88 (t, 3H), 1.46-1.65 (m, 8H), 2.24 (s, 3H), 2.38 (t, J=7.58 Hz, 2H), 4.43 (d, J=4.80 Hz, 2H), 5.37 (s, 1H), 5.93 (s, 1H), 8.23 (d, J=5.81 Hz, 2H), 8.30 (s, 1H), 8.45 (s, 1H), 8.78 (d, J=5.31 Hz, 2H), 9.00 (br. s., 1H), 11.56 (s, 1H).

Workup

filtrationThe reaction mixture was then filtered
washThe collected solid was washed with ethanol
customdried

Sources & evidence

ORD record: ord-7e1fc07212ce4b799b477c6730f20ded
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637509B2

Reaction notes

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