Diisopropylethylamine → HCID 44470247, compound

HRID 1890694Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.CCN(C(C)C)C(C)C.[F:16][C:17]1[CH:18]=[C:19]([C@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:28]2[CH:29]=[CH:30][C:31]3[N:32]([C:34]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([C:43]5[CH:48]=[CH:47][N:46]=[C:45](S(C)(=O)=O)[N:44]=5)[N:38]=4)=[CH:35][N:36]=3)[N:33]=2)[CH:20]=[CH:21][CH:22]=1>CS(C)=O.C(Cl)Cl>[F:16][C:17]1[CH:18]=[C:19]([C@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:28]2[CH:29]=[CH:30][C:31]3[N:32]([C:34]([C:37]4[N:38]=[C:39]([C:43]5[CH:48]=[CH:47][N:46]=[C:45]([N:1]6[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]6)[N:44]=5)[CH:40]=[CH:41][CH:42]=4)=[CH:35][N:36]=3)[N:33]=2)[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In step 14-3, (R)-pyrrolidin-3-ol (136 mg, 1.56 mmol) and DIEA (453 uL, 2.6 mmol) were added to a solution of (R)-6-(2-(3-fluorophenyl)pyrrolidin-1-yl)-3-(6-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yl)imidazo[1,2-b]pyridazine (14-3) (268 mg, 0.52 mmol) in DMSO (3 mL). The mixture was heated to 120° C. for 1 hour. The mixture was diluted with CH2Cl2, washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The mixture was purified by column chromatography (silica gel, CH2Cl2/CH3OH, 5% gradient) to give (R)-1-(4-(6-(6-((R)-2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)pyrimidin-2-yl)pyrrolidin-3-ol (14-4). LC/MS: 523.2 (MH+).

Workup

washwashed with H2O and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe mixture was purified by column chromatography (silica gel, CH2Cl2/CH3OH, 5% gradient)

Sources & evidence

ORD record: ord-3991b1af65e54653b231dc6e07c4ede9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507488B2

Reaction notes

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