5-Cyclopropyl-1,2-oxazole-3-carboxylic acid → (R)-ethyl 3-((1-(5-cyclopropylisoxazole-3-carbonyl)pyrrolidin-2-yl)methoxy)picolinate

HRID 869649Notes

Reaction equation

HRID 869649 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.[CH:19]1([C:22]2[O:26][N:25]=[C:24]([C:27](O)=[O:28])[CH:23]=2)[CH2:21][CH2:20]1.COC1C=C(OC[C@H]2CCCN2C([C@H]2CC[C@H](C(F)(F)F)CC2)=O)C(C(O)=O)=NC=1>>[CH:19]1([C:22]2[O:26][N:25]=[C:24]([C:27]([N:1]3[CH2:5][CH2:4][CH2:3][C@@H:2]3[CH2:6][O:7][C:8]3[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=3)=[O:28])[CH:23]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 3

HCID 10921135-Cyclopropyl-1,2-oxazole-3-carboxylic acidHCID 86666098(R)-ethyl 3-(pyrrolidin-2-ylmethoxy)picolinateHCID 178493765HCID 178493765, compound

Product 1

HCID 86666099(R)-ethyl 3-((1-(5-cyclopropylisoxazole-3-carbonyl)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 5-cyclopropylisoxazole-3-carboxylic 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-f2c7c4fb741448c9a95c46a0b61d967c
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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