2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 118308202, compound

HRID 1750679Notes

Reaction equation

HRID 1750679 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([NH:10][C@H:11]3[CH2:15][CH2:14][CH2:13][C@@H:12]3[NH:16][C:17](=[O:29])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]3[N:28]=[CH:27][CH:26]=[N:25]3)=[N:8][CH:9]=2)C[CH2:2]1.BrC1N=CC(N[C@H]2CCC[C@@H]2NC(=O)C2C=CC=CC=2N2N=CC=N2)=NC=1.ClC1N=CC(N[C@H]2CCC[C@@H]2NC(=O)C2C=CC=CC=2N2N=CC=N2)=NC=1.C(B1OC(C)(C)C(C)(C)O1)=C>>[CH2:1]([C:4]1[N:5]=[CH:6][C:7]([NH:10][C@H:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:24]2[N:25]=[CH:26][CH:27]=[N:28]2)=[N:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 4

HCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 118308077HCID 118308077, compoundHCID 118308312HCID 118308312, compoundHCID 118308320HCID 118308320, compound

Product 1

HCID 118308202HCID 118308202, compound

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-[(5-cyclopropylpyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Example 112) from N-[(1S,2S)-2-[(5-bromopyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide and N-[(1S,2S)-2-[(5-chloropyrazin-2-yl)amino]cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 30a and 30b; 100 mg, 0.23 mmol) and 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS number 75927-49-0; 151 mg, 0.98 mmol) except this was purified only by column chromatography (silica, 0-100% ethyl acetate/petrol) and then was dissolved in ethanol (1.4 ml). To this was then added palladium on carbon (10% wt, 50% wet) (15 mg, 0.014 mmol) and the resulting mixture was stirred under a balloon of hydrogen gas for 2 hours. The reaction was filtered through diatomaceous earth (commercially sold under the trade mark “Celite”) and concentrated in vacuo. This was purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified only by column chromatography (silica, 0-100% ethyl acetate/petrol)
  3. dissolutionwas dissolved in ethanol (1.4 ml)
  4. filtrationThe reaction was filtered through diatomaceous earth (
  5. concentrationconcentrated in vacuo
  6. customThis was purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-422fb477d24645f289c0342590696a62
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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