N,N,N',N'-Tetramethylmethanediamine → HCID 66599777, compound

HRID 1909063Notes

Reaction equation

[C:1]([Si:5]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17]3[NH:19][CH:20]=[N:21][C:16]3=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(=O)OC(=O)CC1.[CH3:47][N:48]([CH3:53])[CH2:49]N(C)C>C(Cl)Cl>[C:1]([Si:5]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17]3[N:19]([CH2:47][N:48]([CH3:53])[CH3:49])[CH:20]=[N:21][C:16]3=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine (4.65 g, 10.2 mmol) in CH2Cl2 (50 mL) was added potassium carbonate (1.60 g, 11.6 mmol, 1.1 eq), succinic anhydride (1.15 g, 11.5 mmol, 1.1 eq) and, N,N,N′,N′-tetramethylmethanediamine (1.6 mL, 11.7 mmol, 1.1 eq) and the resulting suspension stirred for 16 hr at 23° C. The reaction was diluted with CH2Cl2 and washed with 20% NaOH (50 mL), water, dried over Na2SO4, and concentrated to afford {5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-imidazo[4,5-b]pyridin-3-ylmethyl}-dimethyl-amine orange oil (5.13 g, 9.89 mmol, 97%). 1H NMR (400 MHz, CDCl3) δ: 7.81 (s, 1H), 7.72 (d, J=6.0 Hz), 4H), 7.42 (m, 6H), 6.67 (d, J=8.6 Hz, 1H), 4.99 (s, 2H), 4.01 (sept, 1H), 3.91 (m, 2H), 3.38 (m, 2H), 2.38 (s, 6H), 1.68-1.78 (m, 4H), 1.10 (s, 9H).

Workup

washwashed with 20% NaOH (50 mL), water
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-469bd86172b04298b609fe7fc3b3fc47
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598217B2

Reaction notes

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