Isovaleric Acid → HCID 71114476, compound

HRID 710157Notes

Reaction equation

HRID 710157 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:25][C:24]=2[CH:34]=1.[C:35](O)(=[O:40])[CH2:36][CH:37]([CH3:39])[CH3:38].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.O>[F:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[N:18][N:17]=[N:16]2)[CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH:28]3[CH2:29][CH2:30][N:31]([C:35](=[O:40])[CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:32][CH2:33]3)=[N:25][C:24]=2[CH:34]=1

Participants

7

Reactant 4

HCID 10430Isovaleric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 710900805-(2-fluoro-4-(1H-tetrazol-1-yl)phenyl)-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate

Product 1

HCID 71114476HCID 71114476, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

5-[2-fluoro-4-(1H-tetrazol-1-yl)-phenyl]-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate (140 mg, 0.29 mmol) was dissolved in DMF (4 ml) and added isovaleric acid (38 mg, 0.37 mmol), EDC.HCl (147 mg, 0.73 mmol), HOBt (47 mg, 0.35 mmol) and TEA (88 mg, 0.88 mmol). After completion of the reaction, work up (EtOAc/H2O) followed by purification of crude on combiflash using a gradient mixture of EtOAc and Petether (7:3) as eluent afforded the titled compound (100 mg) as a pale-yellow solid. M.P.: 168-172° C. MS (m/z): 449.1 [M+H]+.

Workup

  1. customfollowed by purification of crude on combiflash
  2. additiona gradient mixture of EtOAc and Petether (7:3) as eluent

Sources & evidence

ORD record
ord-c68f17b020c4421194ac71e0eb481bdc
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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