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

HRID 2406807Notes

Reaction equation

HRID 2406807 reaction equation
Cl.Cl.[NH:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[CH2:8][O:9][C:10]1[C:11]([C:16]([NH2:18])=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](O)=[O:25].COC1C=C(OC[C@H]2CCCN2C([C@H]2CC[C@H](C(F)(F)F)CC2)=O)C(C(O)=O)=NC=1>>[F:19][C:20]([F:30])([F:31])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([N:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[CH2:8][O:9][C:10]1[C:11]([C:16]([NH2:18])=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:25]

Participants

4

Reactant 3

HCID 99633-(Trifluoromethyl)benzoic acidHCID 66960633(R)-3-(pyrrolidin-2-ylmethoxy)picolinamide dihydrochlorideHCID 178493765HCID 178493765, compound

Product 1

HCID 66962170(R)-3-((1-(3-(trifluoromethyl)benzoyl)pyrrolidin-2-yl)methoxy)picolinamide

Procedure

The title compound was prepared according to the procedure described in Step 5 of EXAMPLE 31 using (R)-3-(pyrrolidin-2-ylmethoxy)picolinamide dihydrochloride (EXAMPLE 1 Step 3) and 3-(trifluoromethyl)benzoic 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-32a7003cbb204ad0a8b7c439290f9b31
Source dataset
uspto-grants-2014_08
Patent number
US08809380B2

Reaction notes

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