Diisopropylamine → 9-Fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-[(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575411Notes

Reaction equation

HRID 575411 reaction equation
Br[C:2]1[C:3]([F:26])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][C:19]4[N:20]([CH3:24])[N:21]=[CH:22][CH:23]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:25]=1.[CH3:27][C:28]([OH:32])([CH3:31])[C:29]#[CH:30].C(NC(C)C)(C)C>CN(C=O)C>[F:26][C:3]1[C:2]([C:30]#[C:29][C:28]([OH:32])([CH3:31])[CH3:27])=[CH:25][C:6]2[C:7]3[N:8]([C:12]([CH2:18][C:19]4[N:20]([CH3:24])[N:21]=[CH:22][CH:23]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 82582-Methyl-3-butyn-2-olHCID 8669346110-Bromo-9-fluoro-3-[(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

Product 1

HCID 866934629-Fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-[(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamideYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-[(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was prepared similarly according to General Procedure E with slight modification. 10-bromo-9-fluoro-3-[(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-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 2.5 mg (23% yield). M+1=424.2.

Workup

  1. customto afford 2.5 mg (23% yield)

Sources & evidence

ORD record
ord-3187c258dd3e4356b3493811614579f0
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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