Water methylene chloride → HCID 71090081, compound

HRID 710144Notes

Reaction equation

HRID 710144 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(Cl)Cl.O>C(Cl)Cl>[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][NH:31][CH2:32][CH2:33]3)=[N:25][C:24]=2[CH:34]=1

Participants

4

Reactant 2

HCID 21908982Water methylene chlorideHCID 710900805-(2-fluoro-4-(1H-tetrazol-1-yl)phenyl)-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate

Product 1

HCID 71090081HCID 71090081, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-fluoro-4-(1H-tetrazol-1-yl)phenyl]-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate (50 mg) was dissolved in DCM (15 ml) and added TEA (0.3 ml). This mixture stirred for 3 h at rt. Work up (DCM/H2O) followed by purification of the crude by preparative TLC using MeOH and DCM (1:5) as eluent afforded the titled compound (15 mg) as an off-white solid. M.P.: 148-151° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.17 (s, 1H), 8.03 (d, J 9.6, 1H), 7.95-7.79 (m, 4H), 7.58 (d, J 8.5, 1H), 3.22-3.13 (m, 1H), 3.07 (d, J 12.4, 2H), 2.70 (t, J 11.2, 2H), 2.06 (d, J 11.1, 2H), 1.82-1.70 (m, 2H).

Workup

  1. customfollowed by purification of the crude by preparative TLC

Sources & evidence

ORD record
ord-04c53e8a64e543019979e788107a3595
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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