N-Methyloxetan-3-amine → (R)-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-N3-(oxetan-3-ylmethyl)-5,6-dihydrobenzo [f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide

HRID 575229Notes

Reaction equation

HRID 575229 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]([NH:20][CH2:21][CH:22]4[CH2:25][O:24][CH2:23]4)=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1.C(NC(C1N2CCOC3C=CC([C:48]#[C:49][C@@:50]([OH:58])([C:52]4[CH:56]=[C:55]([CH3:57])[O:54][N:53]=4)[CH3:51])=CC=3C2=NC=1C(N)=O)=O)(C)(C)C.CNC1COC1.CC1ON=C([C@](O)(C#C)C)C=1>>[OH:58][C@:50]([C:52]1[CH:56]=[C:55]([CH3:57])[O:54][N:53]=1)([CH3:51])[C:49]#[C:48][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]([NH:20][CH2:21][CH:22]4[CH2:25][O:24][CH2:23]4)=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1

Participants

5

Reactant 4

HCID 46839993N-Methyloxetan-3-amineHCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 8669323710-bromo-N3-(oxetan-3-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamideHCID 86693238(R)-N3-(tert-butyl)-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide

Product 1

HCID 86693236(R)-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-N3-(oxetan-3-ylmethyl)-5,6-dihydrobenzo [f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamideYield 2%

Procedure

Similar to as described in General Procedure G, 10-bromo-N3-(oxetan-3-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide (prepared as described in the synthesis of (R)—N3-(tert-butyl)-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide replacing tert-butyl amine with 3-methylaminooxetane) was reacted with (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol to give the titled compound as an off-white solid (6.7 mg, 2%).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-686532e036ea46f1a81535dbd6a77921
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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