p-Toluenesulfonic acid monohydrate → HCID 56644098, compound

HRID 2370969Notes

Reaction equation

Cl.Cl[C:3]1[N:8]=[C:7]([NH:9][CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[C:6]([F:20])=[CH:5][N:4]=1.[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][C:25]=1[N:31]1[CH:35]=[N:34][N:33]=[N:32]1)([CH3:23])[CH3:22].[OH2:36].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C>[NH3:4].[CH3:3][OH:36].[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:3]2[N:8]=[C:7]([NH:9][CH:10]3[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]3)[C:6]([F:20])=[CH:5][N:4]=2)=[CH:26][C:25]=1[N:31]1[CH:35]=[N:34][N:33]=[N:32]1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-5-fluoro-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidin-4-amine hydrochloride (160 mg, 0.495 mmol, 1 equiv), 4-isopropyl-3-(1H-tetrazol-1-yl)benzenamine (121 mg, 0.594 mmol, 1.2 equiv), and para-toluenesulfonic acid monohydrate (75 mg, 0.396 mmol, 0.8 equiv) in IPA (3 mL) were heated to 100° C. for 3 hours. After cooling to ambient temperature, the crude mixture was quenched with 2M NH3/MeOH followed by concentrating to dryness. The crude product was purified by flash chromatography and eluted with DCM:2M NH3/MeOH (95:5) to provide the desired product (120 mg, 54%) as a white solid.

Workup

temperatureAfter cooling to ambient temperature
customthe crude mixture was quenched with 2M NH3/MeOH
concentrationby concentrating to dryness
customThe crude product was purified by flash chromatography
washeluted with DCM

Sources & evidence

ORD record: ord-d398fb77343749e7b881e46922db8c6b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710223B2

Reaction notes

Loading…