(2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl acetate → HCID 71557629, compound

HRID 1024104Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:21]=[C:15]3[CH2:16][N:17]([CH3:20])[CH2:18][CH2:19][N:14]3[N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C([O:25][CH2:26][C:27]1[C:28]([N:42]2[CH2:54][CH2:53][N:45]3[C:46]4[CH2:47][CH2:48][CH2:49][CH2:50][C:51]=4[CH:52]=[C:44]3[C:43]2=[O:55])=[N:29][CH:30]=[CH:31][C:32]=1B1OC(C)(C)C(C)(C)O1)(=O)C>>[OH:25][CH2:26][C:27]1[C:28]([N:42]2[CH2:54][CH2:53][N:45]3[C:46]4[CH2:47][CH2:48][CH2:49][CH2:50][C:51]=4[CH:52]=[C:44]3[C:43]2=[O:55])=[N:29][CH:30]=[CH:31][C:32]=1[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:21]=[C:15]3[CH2:16][N:17]([CH3:20])[CH2:18][CH2:19][N:14]3[N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1

Participants

Reactant 2

HCID 86684143(2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl acetate

HCID 86684167HCID 86684167, compound

Product 1

HCID 71557629HCID 71557629, compoundYield 10%

Procedure

Following the procedure described in Example 123, and starting with 124g (900 mg, 2.60 mmol) and 3-(acetoxymethyl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-4-ylboronic acid 114e (1.01 g, 2.6 mmol), 124 was obtained as a white solid (147 mg, 10%). MS-ESI: [M+H]+ 565.3. 1H NMR (500 MHz, DMSO-d6) δ 10.02 (s, 1H), 8.56 (d, J=5.0 Hz, 1H), 8.17 (s, 1H), 7.75 (s, 1H), 7.66 (s, 1H), 7.46 (d, J=5.0 Hz, 1H), 6.58 (s, 1H), 6.03 (s, 1H), 4.73 (t, J=5.0 Hz, 1H), 4.62-4.58 (m, 1H), 4.40-4.37 (m, 1H), 4.27-4.19 (m, 2H), 4.10-4.08 (m, 1H), 4.00-3.93 (m, 3H), 3.54 (s, 2H), 2.82 (t, J=5.0 Hz, 2H), 2.64-2.56 (m, 2H), 2.47-2.46 (m, 2H), 2.37 (s, 3H), 1.79-1.68 (m, 4H).

Sources & evidence

ORD record: ord-256ceda1116a4fb2b40d30c441d60945
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722676B2

Reaction notes

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