tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate → (3S,4S)-tert-butyl 3-(3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridin-7-yloxy)-4-hydroxypyrrolidine-1-carboxylate

HRID 79331

Reaction equation

[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22](F)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=2)[N:4]=1)[CH3:2].[OH:33][C@@H:34]1[C@@H:38]([OH:39])[CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35]1.CC(C)([O-])C.[K+]>C1COCC1.CC(O)(C)C>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([O:33][C@@H:34]4[C@@H:38]([OH:39])[CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35]4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=2)[N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (32 mg, 0.075 mmol; prepared as in Example 74, Step A) in THF/t-BuOH (1 mL/1 mL) was added (3S,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate (61 mg, 0.30 mmol) and potassium tert-butoxide (67 mg, 0.60 mmol). The reaction was heated with microwave at 100° C. for 50 minutes, and then concentrated under reduced pressure. Silica gel chromatography (DCM/MeOH 10:1) gave the crude product (42 mg).

Workup

concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c3362d14a019415d972419ceedcbccfe
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Linked notes

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