Triphenylphosphine → methyl (S)-2-(4-benzylpiperazin-1-yl)-3-[4-(2-trifluoromethylpyrazolo[1,5-a]pyridin-3-ylmethoxy)-benzoylamino]propanoate

HRID 517526Notes

Reaction equation

HRID 517526 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]([F:34])([F:33])[C:22]1[C:30]([CH2:31][OH:32])=[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][N:24]2[N:23]=1.[CH2:35]([N:42]1[CH2:47][CH2:46][N:45]([C@@H:48]([CH2:53][NH:54][C:55](=[O:63])[C:56]2[CH:61]=[CH:60][C:59](O)=[CH:58][CH:57]=2)[C:49]([O:51][CH3:52])=[O:50])[CH2:44][CH2:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:35]([N:42]1[CH2:43][CH2:44][N:45]([C@@H:48]([CH2:53][NH:54][C:55](=[O:63])[C:56]2[CH:57]=[CH:58][C:59]([O:32][CH2:31][C:30]3[C:22]([C:21]([F:20])([F:33])[F:34])=[N:23][N:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=34)=[CH:60][CH:61]=2)[C:49]([O:51][CH3:52])=[O:50])[CH2:46][CH2:47]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67056932(2-Trifluoromethylpyrazolo[1,5-a]pyridin-3-yl)methanolHCID 86667918methyl (S)-2-(4-benzylpiperazin-1-yl)-3-(4-hydroxybenzoylamino)propanoate

Product 1

HCID 86667917methyl (S)-2-(4-benzylpiperazin-1-yl)-3-[4-(2-trifluoromethylpyrazolo[1,5-a]pyridin-3-ylmethoxy)-benzoylamino]propanoateYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

795 mg (3.0 mmol) of triphenylphosphine and 565 mg (2.6 mmol) of (2-trifluoromethylpyrazolo[1,5-a]pyridin-3-yl)methanol are added respectively to a solution of 800 mg (2.0 mmol) of methyl (S)-2-(4-benzylpiperazin-1-yl)-3-(4-hydroxybenzoylamino)propanoate (prepared as described in example 22-5) in 8 ml of tetrahydrofuran. After stirring at ambient temperature for 30 min, 595 μl (3.0 mmol) of diisopropyl azodicarboxylate are added and the medium is stirred for 18 h at ambient temperature. After evaporating to dryness, the crude residue obtained is purified by chromatography over a silica column eluted with 100% ethyl acetate. 590 mg (49%) of methyl (S)-2-(4-benzylpiperazin-1-yl)-3-[4-(2-trifluoromethylpyrazolo[1,5-a]pyridin-3-ylmethoxy)-benzoylamino]propanoate are obtained in the form of a light-yellow solid.

Workup

  1. stirringthe medium is stirred for 18 h at ambient temperature
  2. customAfter evaporating to dryness
  3. customthe crude residue obtained
  4. customis purified by chromatography over a silica column
  5. washeluted with 100% ethyl acetate

Sources & evidence

ORD record
ord-290805680d7f4fd28269df5bca8076c8
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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