5-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-piperidin-1-yl}-biphenyl-2-carboxylic acid → 6-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-1-methyl-1H-indole-3-carboxylic acid

HRID 1689794Notes

Reaction equation

HRID 1689794 reaction equation
C1(C2ON=C(C3C(Cl)=CC=CC=3Cl)C=2COC2CCN(C3C=C(C4C=CC=CC=4)C(C(O)=O)=CC=3)CC2)CC1.C[O:41][C:42]([C:44]1[C:52]2[C:47](=[CH:48][C:49]([N:53]3[CH2:59][CH2:58][CH2:57][CH:56]([O:60][CH2:61][C:62]4[C:63]([C:70]5[C:75]([Cl:76])=[CH:74][CH:73]=[CH:72][C:71]=5[Cl:77])=[N:64][O:65][C:66]=4[CH:67]4[CH2:69][CH2:68]4)[CH2:55][CH2:54]3)=[CH:50][CH:51]=2)[N:46]([CH3:78])[CH:45]=1)=[O:43]>>[CH:67]1([C:66]2[O:65][N:64]=[C:63]([C:70]3[C:71]([Cl:77])=[CH:72][CH:73]=[CH:74][C:75]=3[Cl:76])[C:62]=2[CH2:61][O:60][CH:56]2[CH2:57][CH2:58][CH2:59][N:53]([C:49]3[CH:48]=[C:47]4[C:52]([C:44]([C:42]([OH:43])=[O:41])=[CH:45][N:46]4[CH3:78])=[CH:51][CH:50]=3)[CH2:54][CH2:55]2)[CH2:69][CH2:68]1

Participants

3

Reactant 2

HCID 252048335-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-piperidin-1-yl}-biphenyl-2-carboxylic acidHCID 59369340HCID 59369340, compound

Product 1

HCID 252050366-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-1-methyl-1H-indole-3-carboxylic acidYield 61%

Procedure

Following the procedure essentially as described in Example 1, Step 2 for 5-{4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-piperidin-1-yl}-biphenyl-2-carboxylic acid, 6-{4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester (47 mg, 0.083 mmol) provided 28 mg (61%) of the title compound. LC-ES/MS m/z 554.0 (M+1).

Sources & evidence

ORD record
ord-8997c4686dbe4b399ea25cbf1903e103
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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