Water → (R)-6-bromo-4-(1-cyclopropylethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1507957Notes

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.CC[N:17]([CH:21]([CH3:23])[CH3:22])C(C)C.O.CN1C(=O)C[CH2:28][CH2:27]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:17][C@@H:21]([CH:22]3[CH2:28][CH2:27]3)[CH3:23])=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

Reactant 4

HCID 962Water

HCID 13387N-methyl-2-pyrrolidone

HCID 81531Diisopropylethylamine

HCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291753(R)-6-bromo-4-(1-cyclopropylethylamino)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 79%

Procedure

A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (2.0 g, 7.29 mmol), (R)-1-cyclopropylethanamine, HCl (0.975 g, 8.01 mmol) and DIPEA (2.99 mL, 17.12 mmol) in NMP (Volume: 15 mL) was heated to 100° C. for 4 hr. The reaction mixture was added 60 mL of water and stirred for 10 minutes. The solid was collected as the desired product (1.85 g, 79% yield). 1H NMR (400 MHz, CD3OD) δ 8.12 (s, 1H), 7.61 (d, J=1.8 Hz, 1H), 6.95 (d, J=1.8 Hz, 1H), 3.92 (quin, J=6.4 Hz, 1H), 1.40 (d, J=6.4 Hz, 3H), 1.18-1.05 (m, 1H), 0.65-0.49 (m, 2H), 0.41-0.30 (m, 2H). MS (ES+) m/z: 323.1, 325.1 (M+H); HPLC: 93%, retention time: 3.318 min (analytical HPLC Method B).

Sources & evidence

ORD record: ord-48b1e700320745f1a778619289cc8296
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221826B2

Reaction notes

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