(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate → HCID 178448290, compound

HRID 245760Notes

Reaction equation

HRID 245760 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[CH:5][C:4]=1[NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22].Br[C:28]1[N:29]=[C:30]([C@H:38]2[CH2:43][CH2:42][C@H:41]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[CH2:40][CH2:39]2)[N:31]2[CH:36]=[CH:35][N:34]=[C:33]([CH3:37])[C:32]=12>>[C:46]([NH:45][CH2:44][C@H:41]1[CH2:40][CH2:39][C@H:38]([C:30]2[N:31]3[CH:36]=[CH:35][N:34]=[C:33]([CH3:37])[C:32]3=[C:28]([C:7]3[CH:6]=[CH:5][C:4]([NH:18][C:19](=[O:26])[O:20][C@H:21]([CH2:23][CH2:24][CH3:25])[CH3:22])=[C:3]([O:2][CH3:1])[CH:8]=3)[N:29]=2)[CH2:43][CH2:42]1)(=[O:48])[CH3:47]

Participants

3

Reactant 2

HCID 67364014(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamateHCID 178474841HCID 178474841, compound

Product 1

HCID 178448290HCID 178448290, compoundYield 56%

Procedure

(S)-Pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-carbamate (20 mg) and N-(((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methyl)acetamide (20 mg) were reacted according to the procedure described in example 4 step 4c and purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid). Proper fractions were collected and made basic with aqueous sodium hydrogencarbonate, extracted with dichloromethane, organic layer dried (Na2SO4) and concentrated in vacuo to give (S)-pentan-2-yl 4-(3-((trans)-4-(acetamidomethyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenylcarbamate (16 mg).

Workup

  1. custompurified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid)
  2. customProper fractions were collected
  3. extractionextracted with dichloromethane, organic layer
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d87fcf60460465b9962508217c4528b
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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