5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one → 5-(8-(5-(Hydroxymethyl)thiazol-2-ylamino)imidazo[1,2-a]pyrazin-5-yl)isoindolin-1-one

HRID 1684953Notes

Reaction equation

HRID 1684953 reaction equation
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[S:13][C:14]([CH2:17][OH:18])=[CH:15][N:16]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]3[C:33](=[CH:34][CH:35]=2)[C:32](=[O:36])[NH:31][CH2:30]3)O1>>[OH:18][CH2:17][C:14]1[S:13][C:12]([NH:11][C:5]2[C:6]3[N:7]([CH:8]=[CH:9][N:10]=3)[C:2]([C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[C:32](=[O:36])[NH:31][CH2:30]4)=[CH:3][N:4]=2)=[N:16][CH:15]=1

Participants

3

Reactant 2

HCID 219557955-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 57541339(2-(5-Bromoimidazo[1,2-a]pyrazin-8-ylamino)thiazol-5-yl)methanol

Product 1

HCID 251029025-(8-(5-(Hydroxymethyl)thiazol-2-ylamino)imidazo[1,2-a]pyrazin-5-yl)isoindolin-1-one

Procedure

Prepared from the product of Step 2 and Intermediate 4 (5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one) according to the procedure described in Example 1, Step 2. 1H-NMR (400 MHz, d6-DMSO) =4.52 (s, 2H, CH2), 4.67 (d, 2H, CH2), 5.40 (t, 1H, OH), 7.36 (s, 1H, Har), 7.71 (s, 1H, Har), 7.81 (s, 1H, Har), 7.89 (m, 2H, Har), 7.99 (s, 1H, Har), 8.09 (s, 1H, Har), 8.79 (s, 1H, H), 11.61 (s br, 1H, NH). LCMS: Rt 2.04 min (90.0%). MS (MH+, m/z) 379.

Sources & evidence

ORD record
ord-37d3fd8112ac4a2f9e29ffa9f32450de
Source dataset
uspto-grants-2012_04
Patent number
US08148369B2

Reaction notes

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