Triphenylphosphine → HCID 73891112, compound

HRID 2278689Notes

Reaction equation

HRID 2278689 reaction equation
C(C[C@@H]1N(C2C=CC(O[CH:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[C:26]([O:28][CH2:29][CH3:30])[CH:25]=[CH:24][C:23]=4[F:31])[CH2:18][CH2:17]3)=CC=2)N=C(C2C=CC(C#N)=CC=2)[C@H]1C)#N.C([CH2:43][C@@H:44]1[N:48]([C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)[N:47]=[C:46]([C:56]2[CH:63]=[CH:62][C:59]([C:60]#[N:61])=[CH:58][CH:57]=2)[C@H:45]1[CH3:64])#N.C(OC1C=CC(F)=C(N2CCC(O)CC2)C=1)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC([O:105][C:106](/N=N/C(OC(C)(C)C)=O)=[O:107])(C)C>C1COCC1.CCOC(C)=O>[C:60]([C:59]1[CH:62]=[CH:63][C:56]([C:46]2[C@@H:45]([CH3:64])[C@H:44]([CH2:43][C:106]([OH:107])=[O:105])[N:48]([C:49]3[CH:54]=[CH:53][C:52]([O:55][CH:16]4[CH2:17][CH2:18][N:19]([C:22]5[CH:27]=[C:26]([O:28][CH2:29][CH3:30])[CH:25]=[CH:24][C:23]=5[F:31])[CH2:20][CH2:21]4)=[CH:51][CH:50]=3)[N:47]=2)=[CH:57][CH:58]=1)#[N:61]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 86719428HCID 86719428, compoundHCID 867194294-((4S,5S)-5-(cyanomethyl)-1-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl)benzonitrileHCID 86719430HCID 86719430, compound

Product 1

HCID 73891112HCID 73891112, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-((4S,5S)-5-(Cyanomethyl)-1-(4-((1-(5-ethoxy-2-fluorophenyl)piperidin-4-yl)oxy)phenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile: To a stirred solution of 4-((4S,5S)-5-(cyanomethyl)-1-(4-hydroxyphenyl)-4-methyl-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile (310 mg, 0.970 mmol), 1-(5-ethoxy-2-fluorophenyl)piperidin-4-ol (368 mg, 1.492 mmol) and triphenylphosphine (420 mg, 1.585 mmol) in THF (5.8 mL) at rt was added di-tert-butylazodicarboxylate (375 mg, 1.596 mmol). The resulting solution was stirred at rt for 25 h and then evaporated. The residue was purified by two consecutive chromatographies (SiO2, first 95/5 CHCl3/Ether and then 4/1 to 3/2 Hex/EtOAc) to give the desired product (390 mg, 74.0% yield) as a yellow oil: LC-MS [M+H] 538.

Workup

  1. customevaporated
  2. customThe residue was purified by two consecutive chromatographies (SiO2, first 95/5 CHCl3/Ether

Sources & evidence

ORD record
ord-eb37f28a2787448d8703300c8b83bce1
Source dataset
uspto-grants-2015_09
Patent number
US09133163B2

Reaction notes

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