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

HRID 2406800

Reaction equation

HRID 2406800 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.[CH:33]1([C:36]2[O:40][N:39]=[C:38]([C:41](O)=[O:42])[CH:37]=2)[CH2:35][CH2:34]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:33]1([C:36]2[O:40][N:39]=[C:38]([C:41]([N:15]3[CH2:19][CH2:18][CH2:17][C@@H:16]3[CH2:20][O:21][C:22]3[C:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=3)=[O:42])[CH:37]=2)[CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 10921135-Cyclopropyl-1,2-oxazole-3-carboxylic acidHCID 86762606HCID 86762606, compoundHCID 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(trifluoroacetic 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)m ethoxy)picolinic acid.

Sources & evidence

ORD record
ord-39f3c795ce094d46abf200638100145d
Source dataset
uspto-grants-2014_08
Patent number
US08809380B2

Linked notes

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