3-(Trifluoromethyl)benzoic acid → (R)-ethyl 3-((1-(3-(trifluoromethyl)benzoyl)pyrrolidin-2-yl)methoxy)picolinate

HRID 2406802Notes

Reaction equation

HRID 2406802 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH:15]1[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH2:20][O:21][C:22]1[C:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1.[F:33][C:34]([F:45])([F:44])[C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38](O)=[O:39].COC1C=C(OC[C@H]2CCCN2C([C@H]2CC[C@H](C(F)(F)F)CC2)=O)C(C(O)=O)=NC=1>>[F:33][C:34]([F:44])([F:45])[C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38]([N:15]1[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH2:20][O:21][C:22]1[C:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:39]

Participants

4

Reactant 3

HCID 99633-(Trifluoromethyl)benzoic acidHCID 86762606(R)-ethyl 3-(pyrrolidin-2-ylmethoxy)picolinate bis(trifluoroacetic acid) saltHCID 178493765HCID 178493765, compound

Product 1

HCID 86666101(R)-ethyl 3-((1-(3-(trifluoromethyl)benzoyl)pyrrolidin-2-yl)methoxy)picolinate

Procedure

The title compound was prepared according to the procedure described in Step 5 of EXAMPLE 31 using (R)-ethyl 3-(pyrrolidin-2-ylmethoxy)picolinate bis(trifluoroacetic acid) salt (EXAMPLE 34 Step 1) and 3-trifluoromethylbenzoic acid instead of ammonium chloride and 5-methoxy-3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinic acid.

Sources & evidence

ORD record
ord-2294f682c9bd453491d22237a68fe841
Source dataset
uspto-grants-2014_08
Patent number
US08809380B2

Reaction notes

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