Triethylsilane → HCID 178428085, compound

HRID 1421908Notes

Reaction equation

HRID 1421908 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH:8]2[CH2:13][CH:12]3[CH2:14][CH:10]([C:11]3([CH3:16])[CH3:15])[CH:9]2[CH3:17])[C:5](=[CH:18][C:19]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[O:20])[NH:4][C:3]1([CH2:54][C:55]1[N:56]=[CH:57][N:58](CC(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:59]=1)[CH2:29][C:30]1[N:31]=[CH:32][N:33](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:34]=1.[NH4+].[F-].C([SiH](CC)CC)C>C(Cl)Cl>[NH:58]1[CH:59]=[C:55]([CH2:54][C:3]2([CH2:29][C:30]3[N:31]=[CH:32][NH:33][CH:34]=3)[C:2](=[O:1])[N:6]([CH2:7][CH:8]3[CH2:13][CH:12]4[CH2:14][CH:10]([C:11]4([CH3:16])[CH3:15])[CH:9]3[CH3:17])[C:5](=[CH:18][C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=3)=[O:20])[NH:4]2)[N:56]=[CH:57]1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 25516Ammonium fluorideHCID 73458274HCID 73458274, compound

Product 1

HCID 178428085HCID 178428085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound of 1E (0.101 g, 0.108 mmol) in CH2Cl2 (1 ml) was added NH4F (0.010 g, 0.43 mmol) and triethylsilane (0.069 ml, 0.43 mmol) followed by addition of 2 ml TFA. The reaction mixture was stiired at ambient temperature for 12 h. It was partitioned between CH2Cl2 and saturated sodium bicarbonate (NaHCO3) solution. The CH2Cl2 layer was dried over MgSO4, filtered, and concentrated under vacuum to give the crude product. The crude product was chromatographed on silica gel with CH3OH--CHCl3 --NH4OH (6:94:0.1) as eluents to afford the title compound of example 1, 10 mg (0.019 mmol, 19% yield for two steps).

Sources & evidence

ORD record
ord-2012fc96b2e84d8593b9a65da4901dee
Source dataset
uspto-grants-2000_06
Patent number
US06080769

Reaction notes

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