(S)-pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate → HCID 178448288, compound

HRID 245762Notes

Reaction equation

HRID 245762 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].COC(=O)N[CH2:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([C:38]2[N:42]3[CH:43]=[CH:44][N:45]=[C:46]([CH3:47])[C:41]3=[C:40](Br)[N:39]=2)[CH2:34][CH2:33]1>>[CH3:21][O:20][C:19]([CH2:31][C@H:32]1[CH2:33][CH2:34][C@H:35]([C:38]2[N:42]3[CH:43]=[CH:44][N:45]=[C:46]([CH3:47])[C:41]3=[C:40]([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:39]=2)[CH2:36][CH2:37]1)=[O:26]

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 178502113HCID 178502113, compound

Product 1

HCID 178448288HCID 178448288, compoundYield 117.1%

Procedure

(S)-Pentan-2-yl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (19 mg) and methyl((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)methylcarbamate (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-(methoxycarbonylmethyl)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-54cff51c9f64422594586ebd17346b77
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

Loading…