Diisopropylethylamine → HCID 66631894, compound

HRID 711284Notes

Reaction equation

HRID 711284 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([F:17])[CH:12]=2)=[O:10])[CH2:5][CH2:4]1.[F:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][N:26]=2)[CH:22]=[CH:23][CH:24]=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>CN(C=O)C>[F:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][N:14]=1)[C:9]([N:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([F:18])[CH:20]=3)=[N:26][CH:27]=2)[CH2:4][CH2:5]1)=[O:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 247299726-(3-Fluorophenyl)nicotinic acidHCID 67208648HCID 67208648, compound

Product 1

HCID 66631894HCID 66631894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (4-(aminomethyl)piperidin-1-yl)(2-fluoropyridin-4-yl)methanone 93-4 (47 mg, 0.20 mmol), 6-(3-fluorophenyl)nicotinic acid 93-5 (43 mg, 0.20 mmol) and HATU (76 mg, 0.20 mmol) in DMF (1 mL) was added DIEA (0.16 mL, 0.50 mmol). The mixture was stirred at room temperature for 2 hours. The solvent was removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give N-41-(2-fluoroisonicotinoyl)piperidin-4-yl)methyl)-6-(3-fluorophenyl)nicotinamide 93 as a white powder. MS m/z 437.20 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 9.14 (d, 1H, J=1.6 Hz), 8.83 (t, 1H, J=6.0 Hz), 8.39-8.33 (m, 2H), 8.20 (d, 1H, J=8.4 Hz), 8.07-8.00 (m, 2H), 7.65-7.59 (m, 1H), 7.42-7.37 (m, 2H), 7.30 (m, 1H), 4.52 (d, 1H, J=13.2 Hz), 3.45-3.27 (m, 3H), 3.12-3.06 (m, 1H), 2.88-2.84 (m, 1H), 1.94-1.86 (m, 2H), 1.70 (d, 1H, J=12.8 Hz), 1.29-1.22 (m, 2H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-726f8704f1c64dd496bd5d7bdda66531
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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