p-Toluenesulfonic acid monohydrate → HCID 178435596, compound

HRID 475205Notes

Reaction equation

[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH3:34])[CH:17]([C:19]4[CH:33]=[CH:32][C:22]5[N:23](C6CCCCO6)[CH:24]=[N:25][C:21]=5[CH:20]=4)[CH3:18])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO.O>[NH:23]1[C:22]2[CH:32]=[CH:33][C:19]([CH:17]([N:16]([CH3:34])[C:12]3[N:11]=[C:10]([NH:9][C:6]4[CH:5]=[C:4]([CH:1]5[CH2:3][CH2:2]5)[NH:8][N:7]=4)[CH:15]=[CH:14][N:13]=3)[CH3:18])=[CH:20][C:21]=2[N:25]=[CH:24]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 86 (68 mg, 0.148 mmol) in MeOH (50 mL) and water (10 mL) was added TsOH.H2O (44 mg, 0.148 mmol). The reaction mixture was heated at 50° C. for 18 h. The solvent was evaporated in vacuo and the residue was purified by preparative HPLC to afford 25 mg (45%) of (±)-N2-(1-(1H-benzo[d]imidazol-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine (88) as white solid: MS (ESI) m/z=375.3 (M+1).

Workup

customThe solvent was evaporated in vacuo
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-48c4c4c23f7b4e4da2740507dc9f4b92
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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