4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane → N-[(1S,2S)-2-{[3-(Propan-2-yl)-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

HRID 1750675Notes

Reaction equation

HRID 1750675 reaction equation
[CH:1]1([C:4]2[C:5]([NH:14][C@H:15]3[CH2:19][CH2:18][CH2:17][C@@H:16]3[NH:20][C:21](=[O:33])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:28]3[N:32]=[CH:31][CH:30]=[N:29]3)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=2)[CH2:3][CH2:2]1.ClC1C(N[C@H]2CCC[C@@H]2NC(=O)C2C=CC=CC=2N2N=CC=N2)=NC=C(C(F)(F)F)N=1.CC1(C)C(C)(C)OB(C(C)=C)O1.[H][H]>CO.[Pd]>[CH3:3][CH:1]([C:4]1[C:5]([NH:14][C@H:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[NH:20][C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:28]2[N:32]=[CH:31][CH:30]=[N:29]2)=[N:6][CH:7]=[C:8]([C:10]([F:12])([F:13])[F:11])[N:9]=1)[CH3:2]

Participants

7

Reactant 4

HCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 118308153N-[(1S,2S)-2-{[3-Chloro-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide2×HCID 118308162N-[(1S,2S)-2-{[3-Cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 118308270N-[(1S,2S)-2-{[3-(Propan-2-yl)-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-{ [3-cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Example 109) from N-[(1S,2S)-2-{[3-chloro-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 29; 170 mg, 0.38 mmol) and 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (CAS number 126726-62-3; 190 mg, 1.13 mmol) except this was then dissolved in methanol (1.4 ml) and 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 to afford the title compound.

Workup

  1. customPrepared
  2. filtrationThe reaction was filtered through diatomaceous earth (
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fab2588a756d47289620956f9fdee0fe
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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