Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 57805577, compound

HRID 2104243Notes

Reaction equation

HRID 2104243 reaction equation
[Cl:1][C:2]1[C:3]([C:28]([F:31])([F:30])[F:29])=[N:4][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)([C:17](NO)=[NH:18])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=[O:39].C[C@H](NC([C@H]1N(C([C@@H](NC([C@@H](N)CC2C=CC(O)=CC=2)=O)CC(O)=O)=O)CCC1)=O)C(N1[C@H](C(N2[C@H](C(N3[C@H](C(N4[C@H](C(N5[C@H](C(N6[C@H](C(O)=O)CCC6)=O)CCC5)=O)CCC4)=O)CCC3)=O)CCC2)=O)CCC1)=O>>[Cl:1][C:2]1[C:3]([C:28]([F:31])([F:30])[F:29])=[N:4][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)([C:17]([NH2:18])=[O:39])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7]

Participants

4

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 5488810Peptide oostatic hormoneHCID 178427939HCID 178427939, compound

Product 1

HCID 57805577HCID 57805577, compound

Procedure

To the crude material from Example 21 was added 5 mg of CSA and 1 mL of TMOF. The mixture was heated to 100C overnight and the crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent) to yield 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carboxylic acid amide. MS (ES) M+H expected=463.0, found=463.1

Workup

  1. customthe crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-4ca8d7a75320465a8a56ae549d25e55c
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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