Potassium Carbonate → HCID 50907827, compound

HRID 390367Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:32][C:10]3([CH2:15][CH2:14][N:13]([C:16]4[S:17][C:18]([C:21]5[N:22]=[N:23][N:24]([CH2:26][C:27]([O:29]CC)=[O:28])[N:25]=5)=[CH:19][N:20]=4)[CH2:12][CH2:11]3)[CH:9]=2)=[CH:4][CH:3]=1.FC1C=CC(C2C3C(=CC=CC=3)OC3(CCNCC3)C=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:32][C:10]3([CH2:11][CH2:12][N:13]([C:16]4[S:17][C:18]([C:21]5[N:22]=[N:23][N:24]([CH2:26][C:27]([OH:29])=[O:28])[N:25]=5)=[CH:19][N:20]=4)[CH2:14][CH2:15]3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Step 3 Ethyl 2-(5-(2-(4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine]-1′-yl)thiazol-5-yl)-2H-tetrazol-2-yl)acetate In a pressure vial, a mixture of 4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine] (128 mg, 0.433 mmol), Intermediate 4 (175 mg, 0.550 mmol) and K2CO3 (127 mg, 0.919 mmol) were suspended in dry DME (2 mL). The vial was sealed and the mixture was stirred under N2 at an external temperature of 110° C. for 2 h. The reaction mixture was then cooled to room temperature, and diluted with DCM/methanol and concentrated under reduced pressure in the presence of silica gel. The resulting solid residue was purified by Combiflash™ chromatography (SiO2 (12 g), eluting with 3-10% EtOAc/hexanes) to afford the title compound as a solid.

Workup

customThe vial was sealed
temperatureThe reaction mixture was then cooled to room temperature
concentrationconcentrated under reduced pressure in the presence of silica gel
customThe resulting solid residue was purified by Combiflash™ chromatography (SiO2 (12 g), eluting with 3-10% EtOAc/hexanes)

Sources & evidence

ORD record: ord-41d01627b1464ae38aa0fb768c4b16a1
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383643B2

Reaction notes

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