P-Toluenesulfonylhydrazide → 4-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

HRID 1772595Notes

Reaction equation

[Br:1][C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.S(NN)(C1C=CC(C)=CC=1)(=O)=O.CC([O-])=O.[Na+]>COCCOC.O>[Br:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 2b (5.00 g, 10.9 mmol, as prepared in Example 2, Step B) in DME/H2O (10:1 v/v, 150 mL) was added TosNHNH2 (6.41 g, 34.5 mmol) and NaOAc (4.70 g, 57.3 mmol). The reaction mixture was stirred at 80° C. overnight. After cooling to rt, the reaction was quenched with H2O (200 mL). The solids were collected by filtration and washed with Et2O to obtain compound 3a as a white solid (3.50 g, 67% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H20BrN5O: 438.1 (M+H). found: 438.1.

Workup

temperatureAfter cooling to rt
customthe reaction was quenched with H2O (200 mL)
filtrationThe solids were collected by filtration
washwashed with Et2O

Sources & evidence

ORD record: ord-a8e3bb3cc11f46449068d26eb655010f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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