4-Nitrobenzyl bromide → HCID 71536235, compound

HRID 1473235Notes

Reaction equation

HRID 1473235 reaction equation
[C:1]([O:5][CH:6]([C:10]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[NH:18][CH:19]=[CH:20][C:12]=2[C:11]=1[C:21]1[C:22]([CH3:31])=[C:23]2[C:28](=[CH:29][CH:30]=1)[O:27][CH2:26][CH2:25][CH2:24]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[N+:32]([C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1)([O-:34])=[O:33]>CC#N.O>[C:1]([O:5][CH:6]([C:10]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]2[N:18]([CH2:39][C:38]3[CH:41]=[CH:42][C:35]([N+:32]([O-:34])=[O:33])=[CH:36][CH:37]=3)[CH:19]=[CH:20][C:12]=2[C:11]=1[C:21]1[C:22]([CH3:31])=[C:23]2[C:28](=[CH:29][CH:30]=1)[O:27][CH2:26][CH2:25][CH2:24]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 86574196HCID 86574196, compound

Product 1

HCID 71536235HCID 71536235, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared in a manner similar to that described in Example 41 from 2-(tert-butoxy)-2-(6-methyl-4-(5-methylchroman-6-yl)-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetic acid and 4-nitrobenzyl bromide and was isolated by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min) on an achiral column. 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.15-8.23 (m, 2H) 7.31-7.42 (m, 3H) 6.97-7.05 (m, 1H) 6.71-6.80 (m, 1H) 5.80-6.03 (m, 3H) 5.15-5.44 (m, 1H) 4.16-4.26 (m, 2H) 3.61-3.71 (m, 3H) 2.64-2.76 (m, 2H) 2.07-2.16 (m, 2H) 1.93-2.06 (m, 3H) 0.98-1.19 (m, 9H); LCMS (m/z) ES+=560 (M+1).

Sources & evidence

ORD record
ord-806a2c6337f24cdaa239e012f5a45e03
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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