Diisopropylethylamine → N-(5-phenylpyridin-2-yl)-2-(4-(pyridazin-4-yl)phenyl)acetamide

HRID 592135Notes

Reaction equation

HRID 592135 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=2)=[CH:3][N:2]=1.[C:17]1([C:23]2[CH:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:17]1([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:14](=[O:16])[CH2:13][C:10]3[CH:9]=[CH:8][C:7]([C:4]4[CH:5]=[CH:6][N:1]=[N:2][CH:3]=4)=[CH:12][CH:11]=3)=[N:27][CH:28]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1050975-Phenyl-2-pyridinamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584479312-(4-(Pyridazin-4-yl)phenyl)acetic acid

Product 1

HCID 46927799N-(5-phenylpyridin-2-yl)-2-(4-(pyridazin-4-yl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(4-(pyridazin-4-yl)phenyl)acetic acid 37-4 (43 mg, 0.2 mmol), 5-phenylpyridin-2-amine (41 mg, 0.24 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (117 mg, 0.3 mmol) in DMF (1 mL) was added DIEA (104 μL, 0.6 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The crude product was purified by reverse phase HPLC to give N-(5-phenylpyridin-2-yl)-2-2(4-pyridazin-4-yl)phenyl)acetamide 37 as white solid. MS m/z 367.1 (M+1); 1H NMR 400 MHz (CDCl3) δ 9.45-9.44 (m, 1H), 9.22 (dd, 1H, J1=1.2 Hz, J2=11.2 Hz), 8.44 (d, 1H, J=2.4 Hz), 8.29 (d, 1H, J=8.8 Hz), 7.92 (dd, 1H, J1=16.8 Hz, J2=2.4 Hz), 7.70-7.66 (m, 3H), 7.56-7.51 (m, 4H), 7.46-7.43 (m, 2H), 7.39-7.35 (m, 1H), 3.85 (s, 2H).

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-226265fe6fea418b9ec31e292d9a542f
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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