HCID 67362935, compound → HCID 53345312, compound

HRID 245721Notes

Reaction equation

HRID 245721 reaction equation
[F:1][C:2]1[C:3](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:5]([O:25][CH3:26])=[C:6]([NH:8][C:9](=[O:24])[O:10][CH:11]([CH2:13][CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C)C)[CH3:12])[CH:7]=1.Br[C:37]1[N:38]=[C:39]([CH:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)[N:40]2[CH:45]=[CH:44][N:43]=[C:42]([CH3:46])[C:41]=12>>[F:1][C:2]1[C:3]([C:37]2[N:38]=[C:39]([CH:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)[N:40]3[CH:45]=[CH:44][N:43]=[C:42]([CH3:46])[C:41]=23)=[CH:4][C:5]([O:25][CH3:26])=[C:6]([NH:8][C:9](=[O:24])[O:10][CH:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH3:12])[CH:7]=1

Participants

3

Reactant 2

HCID 67362935HCID 67362935, compoundHCID 67364207HCID 67364207, compound

Product 1

HCID 53345312HCID 53345312, compound

Procedure

Reaction of 5-(tert-butyldimethylsilyloxy)pentan-2-yl 5-fluoro-2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (prepared according to the procedures described in example 44, 82 mg) and 1-bromo-8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazine (47.5 mg) according to the procedure described in example 4 step 4c and purification using prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid) gave 5-hydroxypentan-2-yl 5-fluoro-2-methoxy-4-(8-methyl-3-(tetrahydro-2h-pyran-4-yl)imidazo[1,5-a]pyrazin-1-yl)phenylcarbamate (14 mg).

Workup

  1. customprepared
  2. customdescribed in example 4 step 4c and purification

Sources & evidence

ORD record
ord-978b9b0c106a41febe886c83d25d44de
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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