2-Methyl-3-butyn-2-ol → HCID 86693256, compound

HRID 575251Notes

Reaction equation

HRID 575251 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][NH:19][CH:20]4[CH2:23][O:22][CH2:21]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:24]=1.BrC1C=CC2OCCN3C(CN4CCCC4)=C(C(N)=O)N=C3C=2C=1.NC1COC1.[CH3:54][C:55]([OH:59])([C:57]#[CH:58])[CH3:56]>>[OH:59][C:55]([CH3:56])([CH3:54])[C:57]#[C:58][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][NH:19][CH:20]4[CH2:21][O:22][CH2:23]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:24]=1

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 98339233-OxetanamineHCID 8669325310-Bromo-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 8669325710-Bromo-3-((oxetan-3-ylamino)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carb oxamide

Product 1

HCID 86693256HCID 86693256, compoundYield 17%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-((oxetan-3-ylamino)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carb oxamide (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 3-aminooxetane) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a brown solid (17 mg, 17%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-2d1f3a87e3ee42a9b50a07cf68df888f
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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