Diisopropylamine → HCID 86693470, compound

HRID 575417Notes

Reaction equation

HRID 575417 reaction equation
Br[C:2]1[C:3]([F:33])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:19]([OH:31])[C:20]4[N:24]([CH:25]5[CH2:30][CH2:29][CH2:28][CH2:27][O:26]5)[N:23]=[CH:22][CH:21]=4)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:32]=1.[CH3:34][C:35]([OH:39])([CH3:38])[C:36]#[CH:37].C(NC(C)C)(C)C>CN(C=O)C>[F:33][C:3]1[C:2]([C:37]#[C:36][C:35]([OH:39])([CH3:38])[CH3:34])=[CH:32][C:6]2[C:7]3[N:8]([C:13]([CH:19]([OH:31])[C:20]4[N:24]([CH:25]5[CH2:30][CH2:29][CH2:28][CH2:27][O:26]5)[N:23]=[CH:22][CH:21]=4)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=3)[CH:9]3[CH2:12][CH:11]([C:5]=2[CH:4]=1)[CH2:10]3

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 82582-Methyl-3-butyn-2-olHCID 86693469HCID 86693469, compound

Product 1

HCID 86693470HCID 86693470, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Fluoro-3-(hydroxy(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was prepared similarly according to General Procedure E with slight modification. 10-bromo-9-fluoro-3-(hydroxy(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with 3-methyl-1-butyne-3-ol in a solution of DMF (1.3 mL/mmol) and diisopropylamine (2.6 mL/mmol) to afford the title compound which was carried forward to the next step without further purification.

Workup

  1. custom9-Fluoro-3-(hydroxy(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was prepared similarly

Sources & evidence

ORD record
ord-ce328c9c036043f9bff36828ba8a713d
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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