4-Bromo-1H-pyrrolo(3,2-c)pyridine → 4-(1-((9-methyl-6-morpholino-2-(1H-pyrrolo[3,2-c]pyridin-4-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine

HRID 1945724Notes

Reaction equation

HRID 1945724 reaction equation
[CH3:1][N:2]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([Sn](CCCC)(CCCC)CCCC)=[N:6][C:7]=2[N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.Br[C:44]1[C:49]2[CH:50]=[CH:51][NH:52][C:48]=2[CH:47]=[CH:46][N:45]=1>>[CH3:1][N:2]1[C:10]([CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH2:16][CH2:17]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([C:44]1[C:49]3[CH:50]=[CH:51][NH:52][C:48]=3[CH:47]=[CH:46][N:45]=1)=[N:6][C:7]=2[N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 247292174-Bromo-1H-pyrrolo(3,2-c)pyridineHCID 596061644-(1-((9-methyl-6-morpholino-2-(tributylstannyl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine

Product 1

HCID 596058204-(1-((9-methyl-6-morpholino-2-(1H-pyrrolo[3,2-c]pyridin-4-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine

Procedure

Following the procedures to prepare 124, 4-(1-((9-Methyl-6-morpholino-2-(tributylstannyl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine and 4-bromo-1H-pyrrolo[3,2-c]pyridine were reacted to give 133. LCMS: M+H+=518.3. 1H-NMR (400 MHz, DMSO-d6): δ 11.55 (s, 1H), 8.30 (d, 1H), 7.51 (d, 1H), 7.48 (d, 1H), 7.20 (d, 1H), 4.30 (m, 4H), 3.80 (s, 3H), 3.78 (m, 6H), 3.55 (m, 4H), 2.88 (m, 2H), 2.44 (m, 4H), 2.09 (m, 2H), 1.77 (m, 2H), 1.40 (m, 3H)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f30b72109b834e4aa12828674f2c787d
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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