Hydrazine → HCID 46215296, compound

HRID 2367470Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:9]2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26](F)[CH:25]=2)[N:3]=1.CCN(C(C)C)C(C)C.[NH2:42][NH2:43]>CCO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:9]2)[CH:5]=[C:4]([C:24]2[CH:25]=[C:26]3[C:27]([C:30]([NH2:31])=[N:42][NH:43]3)=[CH:28][CH:29]=2)[N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(phenylmethyl)-3-piperidinecarboxamide (190 mg, 0.441 mmol), 3 mL of EtOH, Hunig's base (0.308 ml, 1.761 mmol), and hydrazine anhydrous (0.083 ml, 2.64 mmol) were added, and the yellow mixture was heated at 150° C. for 180 minutes under microwave conditions. The solution turned black. LCMS showed mainly product. The black solids were filtered and the yellow filtrate was evaporated. The resulting yellow residue was dissolved in CH3OH, and EtOAc was used to triturate, affording the title compound (29 mg) as a light yellow solid. LC-MS (ES) m/z=443 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.31-1.52 (m, 1H), 1.61-1.81 (m, 2H), 1.86-2.04 (m, 1H), 2.29-2.45 (m, 1H), 2.77-3.05 (m, 2H), 4.17-4.25 (m, 1H), 4.31-4.69 (m, 3H), 5.38 (s, 2H), 6.09 (s, 2H), 6.58-6.70 (m, 1H), 7.17-7.39 (m, 5H), 7.58 (dd, J=8.6, 1.3 Hz, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.96 (s, 1H), 8.46 (t, J=5.9 Hz, 1H), 11.50 (s, 1H).

Workup

filtrationThe black solids were filtered
customthe yellow filtrate was evaporated
dissolutionThe resulting yellow residue was dissolved in CH3OH
customto triturate

Sources & evidence

ORD record: ord-4877c3d6a5af4831aaed011b632dc908
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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