Diisopropylethylamine → HCID 66648757, compound

HRID 417942Notes

Reaction equation

HRID 417942 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:19](=[O:20])[CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16][C:14]=4[N:15]=3)[C:6]=2[CH:23]=1.Cl[C:25]1[N:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=1.CCN(C(C)C)C(C)C>>[CH3:22][C:17]1([CH3:21])[CH2:16][C:14]2[N:15]=[C:11]([N:7]3[C:6]4[CH:23]=[C:2]([NH:1][C:25]5[N:26]=[N:27][C:28]([CH3:31])=[CH:29][CH:30]=5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)[S:12][C:13]=2[C:19](=[O:20])[CH2:18]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2272543-Chloro-6-methylpyridazine2×HCID 24956161HCID 24956161, compound

Product 1

HCID 66648757HCID 66648757, compoundYield 26.6%

Procedure

A mixture of Example 12 (44 mg, 0.134 mmol), 3-chloro-6-methylpyridazine (15 mg, 0.116 mmol) and DIPEA (0.5 mL, 67.0 mmol) was heated to 180° C. under microwave irradiation for 2 h. A further portion of 3-chloro-6-methylpyridazine (15 mg, 0.116 mmol) was added and heating continued for a further 20 h. The solvent was removed in vacuo and the residue purified by prep HPLC to give the title compound (13 mg, 23%) as a yellow solid. δH (CDCl3) 1.15 (6H, s), 2.42 (2H, s), 2.58 (3H, s), 2.76 (2H, s), 4.13-4.18 (2H, m), 4.32-4.38 (2H, m), 6.93-7.20 (5H, m), 8.03 (1H, d, J 2.4 Hz). LCMS (ES+) 422 (M+H)+.

Workup

  1. temperatureheating
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by prep HPLC

Sources & evidence

ORD record
ord-21fcfb2fd61a417896a480eea61976b0
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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