4-(1-Pyrrolidinyl)piperidine → HCID 178519282, compound

HRID 545438Notes

Reaction equation

HRID 545438 reaction equation
[CH:1]1([N:4]2[C:8]([C:9]([OH:11])=O)=[C:7](C3C=NC(O)=CC=3)[N:6]=[C:5]2C2C=CC(OC(F)(F)F)=CC=2)[CH2:3][CH2:2]1.C(OC(=O)CN(C1CC1)C(=O)[C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][C:44]([F:47])([F:46])[F:45])[CH:38]=1)C.C([O:60][C:61]1[CH:62]=[C:63]([CH:67]=[CH:68][N:69]=1)C(O)=O)C1C=CC=CC=1.[N:70]1([CH:75]2[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]2)[CH2:74][CH2:73][CH2:72][CH2:71]1>>[CH:1]1([N:4]2[C:8]([C:9]([N:78]3[CH2:79][CH2:80][CH:75]([N:70]4[CH2:74][CH2:73][CH2:72][CH2:71]4)[CH2:76][CH2:77]3)=[O:11])=[C:7]([C:63]3[CH:67]=[CH:68][N:69]=[C:61]([OH:60])[CH:62]=3)[N:6]=[C:5]2[C:41]2[CH:42]=[CH:37][CH:38]=[C:39]([O:43][C:44]([F:45])([F:46])[F:47])[CH:40]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 229262722-(Benzyloxy)pyridine-4-carboxylic acidHCID 67132963[Cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl esterHCID 1785240453-Cyclopropyl-5-(6-hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid

Product 1

HCID 178519282HCID 178519282, compound

Procedure

In analogy to the procedure described for example 2, the title compound has been obtained by coupling of 3-cyclopropyl-5-(2-hydroxy-pyridin-4-yl)-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carboxylic acid (prepared in analogy to the sequence described for the preparation of intermediate 9, but using [cyclopropyl-(3-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester instead of [cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester and 2-benzyloxy-isonicotinic acid instead of 6-benzyloxy-nicotinic acid in step 9A) with 4-pyrrolidin-1-yl-piperidine to give the title compound as yellow amorphous solid. MS: 542.2 (MH+).

Workup

  1. customprepared in analogy to the sequence

Sources & evidence

ORD record
ord-f8fe39f426e44947a1b9c06d403c72b0
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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