Phosphorus oxychloride → HCID 11302158, compound

HRID 2374997Notes

Reaction equation

HRID 2374997 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[N:12][C:13]([CH:16]([NH:18][C:19]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=O)[CH3:17])=[CH:14][N:15]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O>ClCCCl>[CH:21]1([C:19]2[N:12]3[C:13]([CH:14]=[N:15][C:10]([NH:9][C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[N:11]3)=[C:16]([CH3:17])[N:18]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58711957HCID 58711957, compound2×

Product 1

HCID 11302158HCID 11302158, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, using N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]cyclohexane-carboxamide (Intermediate 63) (90 mg, 0.25 mmol), 1,2-dichloroethane (5 mL) and phosphorus oxychloride (0.25 mL, 2.68 mmol), to afford 7-cyclohexyl-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (28 mg) as a yellow solid. 1H NMR (DMSO): δ9.46 (s, 1H), 9.06 (s, 1H), 7.71 (d, J=8.7 Hz, 2H), 6.91 (d, J=8.7 Hz, 2H), 3.75 (s, 3H), 3.14 (m, 1H), 2.43 (s; 3H), 1.95 (m, 2H), 1.84 (m, 2H), 1.80-1.60 (m, 3H), 1.51-1.36 (m, 2H), 1.36-1.25 (m,1H).

Sources & evidence

ORD record
ord-2832a9e7ca70482a8b845911e43703cc
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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