1-Bromo-2-methylpropane → HCID 58344511, compound

HRID 1809527Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH2:17][CH2:18][CH:19]4[NH:24][CH2:25][CH2:26][OH:27])[N:11]=2)=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].Br[CH2:35][CH:36]([CH3:38])[CH3:37]>CC(N(C)C)=O>[OH:27][CH2:26][CH2:25][NH:24][CH:19]1[C:20]2[C:16](=[C:15]([C:12]3[N:11]=[C:10]([C:7]4[CH:8]=[CH:9][C:2]([O:1][CH2:35][CH:36]([CH3:38])[CH3:37])=[C:3]([CH:6]=4)[C:4]#[N:5])[O:14][N:13]=3)[CH:23]=[CH:22][CH:21]=2)[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 75 °C

Procedure

Prepared using General Procedure 11. To a solution of 2-hydroxy-5-(3-(1-(2-hydroxyethylamino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)benzonitrile 102 (15.0 mg, 0.041 mmol) in DMA (2 mL) was added K2CO3 (16.9 mg, 0.12 mmol) and 1-bromo-2-methylpropane (11.3 mg, 0.08 mmol). The mixture was stirred 6 h at 75° C. The solvent was evaporated and the mixture was partitioned between EA and brine. The organic layer was dried over MgSO4, filtered, and the solvent evaporated. The final compound was purified by preparative HPLC to give 6.31 mg (37%) of 5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isobutoxybenzonitrile 103 as a white solid. LCMS-ESI (m/z) calculated for C24H16N4O3: 418.5; found 419.2 [M+H]+, tR=2.61 min.

Workup

customPrepared
customThe solvent was evaporated
customthe mixture was partitioned between EA and brine
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customthe solvent evaporated
customThe final compound was purified by preparative HPLC

Sources & evidence

ORD record: ord-98ce4727ba9044878912f0dfb0f43009
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362048B2

Reaction notes

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