Diisopropylethylamine → HCID 71537060, compound

HRID 1473231Notes

Reaction equation

HRID 1473231 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].Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.CCN(C(C)C)C(C)C>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]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5642092-(Bromomethyl)pyridineHCID 86574196HCID 86574196, compound

Product 1

HCID 71537060HCID 71537060, 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 2-(bromomethyl)pyridine, except that Hunig's base (10 eq.) was used instead of cesium carbonate 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 8.75-8.91 (m, 1H) 8.14-8.27 (m, 1H) 7.85-8.01 (m, 1H) 7.62-7.75 (m, 1H) 7.30-7.42 (m, 1H) 6.68-6.80 (m, 1H) 6.38-6.47 (m, 2H) 5.80-6.03 (m, 2H) 5.25-5.54 (m, 1H) 4.15-4.28 (m, 2H) 3.68 (s, 3H) 2.61-2.74 (m, 2H) 2.06-2.16 (m, 2H) 1.89-2.02 (m, 3H) 1.04 (s, 9H); LCMS (m/z) ES+=516 (M+1).

Sources & evidence

ORD record
ord-0b460c24c7394377a765df5e0fb1f32a
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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