Ethyl Acetate → HCID 178428224, compound

HRID 1091814Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.[Cl:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[C:11]([S:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:25])=[CH:19][CH:18]=2)[N:10]=1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>CN(C)C=O>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:13]2[CH:14]=[C:9]([Cl:8])[N:10]=[C:11]([S:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30]4)=[O:25])=[CH:19][CH:18]=3)[N:12]=2)[NH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-methyl-1H-pyrazol-5-amine (160 mg, 1.63 mmol) and N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)cyclopentane carboxamide (600 mg, 1.63 mmol) in dimethyl formamide (10 ml) was added diisopropylethylamine (248 mg, 1.96 mmol, 0.34 ml). The mixture was then heated to 80° C. for 18 hrs and allowed to cool to rt. EtOAc (40 ml) was added and washed with brine, dried (MgSO4), and concentrated in vacuo. Crude product was then purified by flash chromatography 7:3 EtOAc:hexane EtOAc 5% MeOH:EtOAc to give title compound as an off white solid (431 mg, 62%). 1H NMR (DMSO-d6) 1.50-1.55 (2H, m), 1.61-1.78 (4H, m), 1.79-1.85 (2H, m), 1.90 (3H, brs), 2.72-1.81 (1H, m), 5.21 (1H, brs), 6.46 (1H, brs), 7.52 (2H, d), 7.78 (2H, d), 10.11 (1H, s), 10.18 (1H, brs), 11.95 (1H, brs). ES+ 429.

Workup

temperatureto cool to rt
washwashed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customCrude product was then purified by flash chromatography 7:3 EtOAc

Sources & evidence

ORD record: ord-747158362d4e449e95732c8876bb0fb2
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129399B2

Reaction notes

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