Tert-butyl 3-iodoazetidine-1-carboxylate → 1-(azetidin-3-yl)-4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

HRID 874005Notes

Reaction equation

HRID 874005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][NH:12][C:11]=3[C:10](=[O:17])[N:9]2[C:18]2[CH:19]=[C:20]([CH3:28])[C:21]3[N:22]([C:24]([CH3:27])=[N:25][N:26]=3)[CH:23]=2)=[CH:4][CH:3]=1.I[CH:30]1[CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]1>>[NH:32]1[CH2:33][CH:30]([N:12]2[C:11]3[C:10](=[O:17])[N:9]([C:18]4[CH:19]=[C:20]([CH3:28])[C:21]5[N:22]([C:24]([CH3:27])=[N:25][N:26]=5)[CH:23]=4)[CH:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[C:15]=3[C:14]([CH3:16])=[N:13]2)[CH2:31]1

Participants

3

Reactant 2

HCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 178434164HCID 178434164, compound

Product 1

HCID 918263501-(azetidin-3-yl)-4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Conditions

Temperature
80 °C

Procedure

The title compound was prepared using an analogous procedure to that described in Example 134 using 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 98) (750 mg, 1.909 mmol) and stirring the reaction mixture for 30 min at 80° C. after addition of tert-butyl 3-iodoazetidine-1-carboxylate. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-4%) followed by preparative HPLC (Gilson gx-281. Column: Sunfire C18, 30×100 mm, 5 μm. Flow: 30 mL/min. Gradient: 5% to 60% B in 20 min; A=0.1% TFA in H2O, B=CH3CN. Detection: UV) to afford:

Workup

  1. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 1-4%)
  2. waitGradient: 5% to 60% B in 20 min
  3. customDetection: UV) to afford

Sources & evidence

ORD record
ord-0673b404d32c4435b5a72f4788d981fc
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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