2-Methyl-3-butyn-2-ol → HCID 86693268, compound

HRID 575257Notes

Reaction equation

HRID 575257 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][N:19]4[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1.BrC1C=CC2OCCN3C(CN4CCCC4)=C(C(N)=O)N=C3C=2C=1.CN1CCNCC1.[CH3:58][C:59]([OH:63])([C:61]#[CH:62])[CH3:60]>>[OH:63][C:59]([CH3:60])([CH3:58])[C:61]#[C:62][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][N:19]4[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 531671-MethylpiperazineHCID 8669325310-Bromo-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 86693269HCID 86693269, compound

Product 1

HCID 86693268HCID 86693268, compoundYield 23%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-((4-methylpiperazin-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide (prepared similarly as described in the synthesis of 10-bromo-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide replacing pyrrolidine with N-methylpiperazine) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a colorless solid (12 mg, 23%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-f716a4ad3e144f2daf506b5740b061aa
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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