Hydrochloric Acid → HCID 9879961, compound

HRID 2181617Notes

Reaction equation

[CH3:1][N:2]([CH3:29])[S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([CH:18]([O:20]CC3C=CC=CC=3)[CH3:19])[N:15]=[C:14](Cl)[N:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4].Cl.C([O-])=O.[NH4+]>C(O)(C)C>[CH3:29][N:2]([CH3:1])[S:3]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([CH:18]([OH:20])[CH3:19])[N:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-[4-(1-benzyloxy-ethyl)-6-chloro-[1,3,5]triazin-2-yl]-piperazine-1-sulfonic acid dimethylamide (0.73 mmol, 320 mg), (Pd—C 910%, 640 mg), HCl (2 M in ether, 4.4 mmol, 2.2 mL), ammonium formate (15 mmol, 915 mg) and isopropanol (10 mL) was heated at 90° C. for 2 h. The reaction was cooled and filtered, and to the filtrate was added chloroform (20 mL) and aq. saturated sodium bicarbonate (20 mL). The chloroform layer was collected, dried, filtered and the filtrate was evaporated to dryness. The resulting residue was purified by silica gel chromatography (eluent, 96:4 chloroform-methanol) to yield the title compound of this example (59%, 136 mg); mp 124-125° C.; NMR 1.5 (d, 3H), 2.8 (s, 6H), 3.3 (m, 4H), 4.0 (s, 4H0, 7.2 (s, 1H, 8.6 (s, 1H).

Workup

temperatureThe reaction was cooled
filtrationfiltered
additionto the filtrate was added chloroform (20 mL) and aq. saturated sodium bicarbonate (20 mL)
customThe chloroform layer was collected
customdried
filtrationfiltered
customthe filtrate was evaporated to dryness
customThe resulting residue was purified by silica gel chromatography (eluent, 96:4 chloroform-methanol)

Sources & evidence

ORD record: ord-ce7987b2661c45b0b77ea3f59b472186
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894047B2

Reaction notes

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