Hydrochloric Acid → 3-[5'-ethynyl-2'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,4']-bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 74686Notes

Reaction equation

HRID 74686 reaction equation
[F-].[CH2:2]([N+](CCCC)(CCCC)CCCC)[CH2:3]CC.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([C:29]([C:31]1[CH:36]=[C:35]([N:37]3[CH2:42][CH2:41][CH:40]([N:43]4[CH2:49][CH2:48][C:47]5[CH:50]=[C:51]([O:54][CH3:55])[CH:52]=[CH:53][C:46]=5[NH:45][C:44]4=[O:56])[CH2:39][CH:38]3C#C)[C:34]([Si](C)(C)C)=[CH:33][N:32]=1)=[O:30])[CH2:24][CH2:23]2.Cl>C1COCC1>[C:2]([C:34]1[C:35]([N:37]2[CH2:38][CH2:39][CH:40]([N:43]3[CH2:49][CH2:48][C:47]4[CH:50]=[C:51]([O:54][CH3:55])[CH:52]=[CH:53][C:46]=4[NH:45][C:44]3=[O:56])[CH2:41][CH2:42]2)=[CH:36][C:31]([C:29]([N:25]2[C:26]3[C:22](=[CH:21][C:20]([F:19])=[CH:28][CH:27]=3)[CH2:23][CH2:24]2)=[O:30])=[N:32][CH:33]=1)#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 131731844HCID 131731844, compound

Product 1

HCID 426130623-[5'-ethynyl-2'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,4']-bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

86 μL (86 μmol) of a 1N tetrabutylammonium fluoride solution in THF were added to 35 mg (57 mol) 3-[2′-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-5′-trimethylsilanyl-ethynyl-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]-diazepin-2-one in 1.5 mL THF and the mixture was stirred for 3 h at RT. Then the reaction mixture was combined with a 0.1 molar aqueous hydrochloric acid solution and the precipitate formed was suction filtered.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-b8a5b6289fa14eb79c2ac3f773f2451f
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

Loading…