HCID 58073128, compound → HCID 44218899, compound

HRID 1469368

Reaction equation

HRID 1469368 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:13][CH:12]([O:14][C:15]3[CH:20]=[CH:19][C:18](I)=[CH:17][N:16]=3)[CH2:11]2)=[O:9])[N:2]=1.[CH2:22]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:34]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:36]=[CH:37][CH:38]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:13][CH:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:35]4[CH:36]=[CH:37][CH:38]=[C:33]([O:32][CH2:31][CH2:30][O:29][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:34]=4)=[CH:17][N:16]=3)[CH2:11]2)=[O:9])[N:2]=1

Participants

3

Reactant 2

HCID 58073128HCID 58073128, compoundHCID 66710496US10918640, Example 14

Product 1

HCID 44218899HCID 44218899, compoundYield 28%

Procedure

This compound was prepared by the method outlined for example 5 step 6. Thus 3-(5-iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid pyridazin-3-ylamide (example 7, step 1) (600 mg, 1.15 mmol) was reacted with 2-[3-(2-benzyloxy-ethoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.5 equiv). Crude product purified by flash chromatography on silica gel eluting with 4:1 ethyl acetate:hexane to afford title compound (214 mg, 28%) as a brown foam.

Workup

  1. customThis compound was prepared by the method
  2. customCrude product purified by flash chromatography on silica gel eluting with 4:1 ethyl acetate

Sources & evidence

ORD record
ord-2a1ba5558fc04308a8d5c86791ef02c9
Source dataset
uspto-grants-2015_04
Patent number
US09006269B2

Linked notes

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