Diisopropylethylamine → HCID 68291929, compound

HRID 1507989Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.Cl.[NH2:16][C@H:17]([CH3:24])[C:18]([CH3:23])([CH3:22])[C:19]([NH2:21])=[O:20].CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:21][C:19](=[O:20])[C:18]([CH3:23])([CH3:22])[C@H:17]([NH:16][C:9]1[C:4]2[N:5]([CH:14]=[C:2]([Br:1])[CH:3]=2)[N:6]=[CH:7][C:8]=1[C:11]([NH2:13])=[O:12])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (400 mg, 1.457 mmol) in DMF (30 mL) was added (R)-3-amino-2,2 dimethylbutanamide hydrochloride (486 mg, 2.91 mmol) and DIPEA (1.273 ml, 7.29 mmol) at RT and the reaction mixture was allowed to stir at 100° C. for 12 h. It was then quenched with water (300 ml) and extracted with EtOAc (3×150 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. Crude product was purified by combi-flash (12 g silica column, 85% EtOAc: Pet-Ether) to afford an off white solid (380 mg, 70.8% yield). 1HNMR (400 MHz, DMSO) δ ppm: 1.13-1.18 (m, 9H), 4.51-4.55 (d, J=16 Hz, 1H), 6.98 (s, 3H), 7.05-7.05 (d, J=1.6 Hz, 1H), 7.272 (s, 1H), 7.88-7.89 (d, J=4.0 Hz, 1H), 8.236 (s, 1H), 10.88-10.90 (d, J=8.0 Hz 1H).

Workup

customIt was then quenched with water (300 ml)
extractionextracted with EtOAc (3×150 mL)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated under vacuum
customCrude product was purified by combi-flash (12 g silica column, 85% EtOAc: Pet-Ether)

Sources & evidence

ORD record: ord-91c497fc37f44199aa8e0d5f4a3f6e49
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221826B2

Reaction notes

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