Triethylamine → HCID 66547153, compound

HRID 1507916Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16]([NH:17][C@H:18]([CH3:23])[C:19]([F:22])([CH3:21])[CH3:20])=[C:15]([C:24]([NH2:26])=[O:25])[CH:14]=[N:13][N:12]3[CH:27]=2)[CH:6]=[CH:7][CH:8]=1.[C:28]([N:35]1[CH:39]=[CH:38]N=C1)(N1C=CN=C1)=[O:29].[CH3:40]CN(CC)CC.C1(N)CC1>C(Cl)CCl>[CH:39]1([NH:35][C:28]([NH:1][CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:10]=[C:11]4[C:16]([NH:17][C@H:18]([CH3:23])[C:19]([F:22])([CH3:21])[CH3:20])=[C:15]([C:24]([NH2:26])=[O:25])[CH:14]=[N:13][N:12]4[CH:27]=3)[CH:6]=[CH:7][CH:8]=2)=[O:29])[CH2:38][CH2:40]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (R)-6-(3-(aminomethyl)phenyl)-4-(3-fluoro-3-methylbutan-2-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (Example 68, 18.5 mg, 0.050 mmol), 1,1′-carbonyldiimidazole (16.24 mg, 0.100 mmol), and Et3N (0.017 mL, 0.125 mmol) in C1CH2CH2Cl (1 mL) was stirred at 23° C. for 1 hr then cyclopropanamine (8.67 μl, 0.125 mmol) was added and the resulting mixture was heated to 80° C. for 30 minutes. The reaction was cooled, concentrated and redissolved in 1 mL of MeOH with a few drops of DMF. The reaction mixture was purified by reverse-phase preparative HPLC (condition C) to yield the title compound (14.2 mg, 61%). HPLC (condition H): retention time=1.42 minute. LC/MS (M+H)+=453.4.

Workup

temperatureThe reaction was cooled
concentrationconcentrated
dissolutionredissolved in 1 mL of MeOH with a few drops of DMF
customThe reaction mixture was purified by reverse-phase preparative HPLC (condition C)

Sources & evidence

ORD record: ord-81cafa32c19f4722aa5b37df77b5d331
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221826B2

Reaction notes

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