Triphenylphosphine → Cyclopropanesulphonic acid {17-[2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carbonyl)-amide

HRID 2242458Notes

Reaction equation

HRID 2242458 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH:16]1[CH2:33][CH:32]2[CH:18]([C:19](=[O:45])[N:20]([CH3:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH:27]3[C:29]([C:35]([NH:37][S:38]([CH:41]4[CH2:43][CH2:42]4)(=[O:40])=[O:39])=[O:36])([NH:30][C:31]2=[O:34])[CH2:28]3)[CH2:17]1.[CH:46]([C:49]1[N:50]=[C:51]([C:54]2[CH:63]=[C:62](O)[C:61]3[C:56](=[CH:57][C:58]([O:65][CH3:66])=[CH:59][CH:60]=3)[N:55]=2)[S:52][CH:53]=1)([CH3:48])[CH3:47].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH:46]([C:49]1[N:50]=[C:51]([C:54]2[CH:63]=[C:62]([O:15][CH:16]3[CH2:33][CH:32]4[CH:18]([C:19](=[O:45])[N:20]([CH3:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH:27]5[C:29]([C:35]([NH:37][S:38]([CH:41]6[CH2:42][CH2:43]6)(=[O:40])=[O:39])=[O:36])([NH:30][C:31]4=[O:34])[CH2:28]5)[CH2:17]3)[C:61]3[C:56](=[CH:57][C:58]([O:65][CH3:66])=[CH:59][CH:60]=3)[N:55]=2)[S:52][CH:53]=1)([CH3:48])[CH3:47]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 72539645Cyclopropanesulphonic acid (17-hydroxy-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carbonyl)-amideHCID 178487691HCID 178487691, compound

Product 1

HCID 72774609Cyclopropanesulphonic acid {17-[2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carbonyl)-amideYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (22 uL, 0.11 mmol) was added to a mixture of the metathesis product 103 (23 mg), 2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxyquinolin-4-ol (24 mg, 0.08 mmol), and PPh3 (30 mg, 0.11 mmol) in 1 mL dry THF, in an ice bath. The mixture was stirred at rt overnight and then evaporated. The residue (1.2 mL of a 1.5-mL MeCN solution) was purified by prep-HPLC (Hypercarb 7 uL 100×21.2 mm, 40% to 99% aqueous MeCN in 10 min) to give 3.18 mg MV062308 as cream solids (13% yield).

Workup

  1. customevaporated
  2. customThe residue (1.2 mL of a 1.5-mL MeCN solution) was purified by prep-HPLC (Hypercarb 7 uL 100×21.2 mm, 40% to 99% aqueous MeCN in 10 min)
  3. customto give 3.18 mg

Sources & evidence

ORD record
ord-3345941ee39144018b3425cda7ca1245
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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