Formic Acid → HCID 136623158, compound

HRID 1482928Notes

Reaction equation

[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13]2[N:18]=[C:17]([NH2:19])[C:16]([O:20]C)=[CH:15][N:14]=2)=[N:6]1.C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1.C(O)=O>CN1CCCC1=O>[NH2:19][C:17]1[C:16]([OH:20])=[CH:15][N:14]=[C:13]([C:7]2[C:8]3[CH2:12][CH2:11][CH2:10][C:9]=3[N:5]([CH2:4][C:3]3[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=3[F:1])[N:6]=2)[N:18]=1

Participants

Conditions

Temperature: 190 °C

Procedure

5.61 g of 2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5-methoxypyrimidin-4-amine 1-4-2 (16.5 mmol, 1.00 eq) were dissolved in 680 mL of dry 1-methylpyrrolidin-2-one. 1.14 g of potassium carbonate (8.27 mmol, 0.5 eq.), and 3.40 mL benzenethiol (33.1 mmol, 2.0 eq.) were added. The mixture was stirred for 0.5 h at 190° C. bath temperature. Then the reaction mixture was partitioned between aqueous half saturated ammonium chloride solution and ethyl DCM/isopropanol (4:1). The organic layer was dried with magnesium sulfate and concentrated in vacuo. The purification of the residue by flash chromatography provided 6.60 g (17.0 mmol, 100%) of the target compound without formic acid. Further purification of 170 mg by HPLC resulted in analytically pure target compound: 53 mg.

Workup

customThen the reaction mixture was partitioned between aqueous half saturated ammonium chloride solution and ethyl DCM/isopropanol (4:1)
dry with materialThe organic layer was dried with magnesium sulfate
concentrationconcentrated in vacuo
customThe purification of the residue by flash chromatography

Sources & evidence

ORD record: ord-bcd40eaaae53433e874da25f56cbaf36
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416125B2

Reaction notes

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