Tetrahydrofuran → 4'-({4-[1-(4-Hydroxyphenyl)piperidin-4-yl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

HRID 519760Notes

Reaction equation

HRID 519760 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:26](=[O:27])[C:25]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([C:35]5[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=5)=[CH:31][CH:30]=4)=[C:24]([CH2:43][CH2:44][CH3:45])[N:23]4[N:46]=[CH:47][N:48]=[C:22]34)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.O1CCCC1>[C].[Pd].CO>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:16][CH2:17][CH:18]([N:21]3[C:26](=[O:27])[C:25]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([C:35]5[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=5)=[CH:31][CH:30]=4)=[C:24]([CH2:43][CH2:44][CH3:45])[N:23]4[N:46]=[CH:47][N:48]=[C:22]34)[CH2:19][CH2:20]2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 670089694'-[(4-{1-[4-(Benzyloxy)phenyl]piperidin-4-yl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

Product 1

HCID 670084854'-({4-[1-(4-Hydroxyphenyl)piperidin-4-yl]-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4′-[(4-{1-[4-(benzyloxy)phenyl]piperidin-4-yl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (364 mg), 10% palladium-carbon (containing water by 50%, 91 mg), tetrahydrofuran (10 mL) and methanol (10 mL) was stirred at room temperature for 16 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the solvent was evaporated. The residue was purified by preparative HPLC [eluent: 0.1% trifluoroacetic acid-containing acetonitrile/0.1% trifluoroacetic acid-containing water=5/95→100/0 (volume ratio)] to give the title compound as a colorless amorphous compound (183 mg, 59%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. customThe residue was purified by preparative HPLC [eluent: 0.1% trifluoroacetic acid-containing acetonitrile/0.1% trifluoroacetic acid-containing water=5/95→100/0 (volume ratio)]

Sources & evidence

ORD record
ord-1b2b9524d8ff400191a395f31dff838e
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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