Triphenylphosphine → HCID 56847526, compound

HRID 1467384Notes

Reaction equation

HRID 1467384 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21]3[C:20]4[CH:19]=[C:18]([O:22][CH:23]([C:35]5[S:36]C=C[CH:39]=5)CNC(=O)OCC[Si](C)(C)C)[C:17]([O:40][CH3:41])=[CH:16][C:15]=4[N:14]=[CH:13][C:12]=3[N:11]([CH3:42])[C:10]2=[O:43])=[C:5]([F:44])[CH:4]=1)#[N:2].FC1C=C(C=CC=1N1C2C3C=C(O)C(OC)=CC=3N=CC=2N(C)C1=O)[C:49]#[N:50].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.S1C(CO)=CN=C1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[F:44][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[N:9]1[C:21]2[C:20]3[CH:19]=[C:18]([O:22][CH2:23][C:35]4[S:36][CH:49]=[N:50][CH:39]=4)[C:17]([O:40][CH3:41])=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]([CH3:42])[C:10]1=[O:43])[C:1]#[N:2]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27632165-ThiazolylmethanolHCID 66611737HCID 66611737, compoundHCID 86689178HCID 86689178, compound

Product 1

HCID 56847526HCID 56847526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For the preparation, see also synthesis of 2-trimethylsilanylethyl {2-[1-(4-cyano-2-fluorophenyl)-7-methoxy-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yloxy]-2-thiophen-2-ylethyl}carbamate under Example 3b: 3-fluoro-4-(8-hydroxy-7-methoxy-3-methyl-2-oxo-2,3-dihydroimidazo[4,5-c]quinolin-1-yl)benzonitrile (63 mg, 173 μmol), triphenylphosphine (polymer-bound) (294 mg, 1.12 mmol), thiazol-5-ylmethanol (62 mg, 540 μmol), diisopropyl azodicarboxylate (166 μl, 845 μmol) in tetrahydrofuran (7 ml) were reacted, giving 3-fluoro-4-[7-methoxy-3-methyl-2-oxo-8-(thiazol-5-ylmethoxy)-2,3-dihydroimidazo-[4,5-c]quinolin-1-yl]benzonitrile (15 mg, 32.5 μmol) as solid. MS: 462.0 (M+H+), TLC (HPTLC): Rf=0.44 (ethyl acetate/ethanol 2:1, parts by volume).

Workup

  1. customFor the preparation

Sources & evidence

ORD record
ord-a606713949f147179f7eab8b168569f1
Source dataset
uspto-grants-2015_04
Patent number
US09000153B2

Reaction notes

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