1-Chloro-4-phenylphthalazine → HCID 59427310, compound

HRID 1013679Notes

Reaction equation

HRID 1013679 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]([NH2:18])=[O:17])[S:15][C:8]=23)=[CH:4][CH:3]=1.Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:24][N:23]=1>C(O)(C)(C)C>[C:32]1([C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22]([NH:1][C:2]3[CH:20]=[CH:19][C:5]([O:6][C:7]4[CH:12]=[CH:11][N:10]=[C:9]5[CH:13]=[C:14]([C:16]([NH2:18])=[O:17])[S:15][C:8]=45)=[CH:4][CH:3]=3)=[N:23][N:24]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 2721091-Chloro-4-phenylphthalazineHCID 67317411HCID 67317411, compound

Product 1

HCID 59427310HCID 59427310, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A 5 ml microwave tube was charged with 7-(4-aminophenoxy)thieno[3,2-b]pyridine-2-carboxamide (85 mg, 0.300 mmol) and 1-chloro-4-phenylphthalazine (60 mg, 0.250 mmol) in 2.0 ml of tert-butanol. The vessel was capped and irradiated at 140° C. for 15 minutes in the microwave. Analysis of an aliquot of the crude mixture by LCMS showed remaining starting material and approximately 20% conversion to desired product. Irradiated at 150° C. for an additional 20 minutes, at which time reaction was deemed complete by LCMS analysis. Cooled to ambient temperature and diluted reaction mixture with methanol. Filtered solids, washed with additional methanol and concentrated in vacuo to afford 7-(4-(4-phenylphthalazin-1-ylamino)phenoxy)thieno[3,2-b]pyridine-2-carboxamide. MS m/z=490 [M+H]+. Calc'd for C28H19N5O2S: 489.55.

Workup

  1. customThe vessel was capped
  2. customirradiated at 140° C. for 15 minutes in the microwave

Sources & evidence

ORD record
ord-013ee7cf5bb84e16be9a0a1ad1722512
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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