2-(4,4-Difluorocyclohexyl)acetic acid → (R)-ethyl 3-((1-(2-(4,4-difluorocyclohexyl)acetyl)pyrrolidin-2-yl)methoxy)picolinate

HRID 869650Notes

Reaction equation

HRID 869650 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][O:7][C:8]1[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1.[F:19][C:20]1([F:30])[CH2:25][CH2:24][CH:23]([CH2:26][C:27](O)=[O:28])[CH2:22][CH2:21]1.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]1([F:30])[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([N:1]2[CH2:5][CH2:4][CH2:3][C@@H:2]2[CH2:6][O:7][C:8]2[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:28])[CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 534207432-(4,4-Difluorocyclohexyl)acetic acidHCID 86666098(R)-ethyl 3-(pyrrolidin-2-ylmethoxy)picolinateHCID 178493765HCID 178493765, compound

Product 1

HCID 86666100(R)-ethyl 3-((1-(2-(4,4-difluorocyclohexyl)acetyl)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(trifuluoroacetic acid) salt (EXAMPLE 34 Step 1) and 2-(4,4-difluorocyclohexyl)acetic 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-d355c87fac6f41028427b523bafac5fe
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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