1,3-Benzodioxole, 5-(chloromethyl)- → 2-(1-(benzo[d][1,3]dioxol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid

HRID 1473222Notes

Reaction equation

HRID 1473222 reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[NH:19][CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH2:29]1[O:39][C:38]2[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][C:31]=2[O:30]1>>[O:39]1[C:38]2[CH:37]=[CH:36][C:33]([CH2:34][N:19]3[C:14]4[C:15](=[O:18])[N:16]([CH3:17])[C:11]([CH:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[C:7]([OH:9])=[O:8])=[C:12]([C:22]5[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=5)[C:13]=4[CH:21]=[CH:20]3)=[CH:32][C:31]=2[O:30][CH2:29]1

Participants

3

Reactant 2

HCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 89462627methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

Product 1

HCID 715370582-(1-(benzo[d][1,3]dioxol-5-ylmethyl)-6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid

Procedure

The title compound was prepared in a manner similar to that described in Example 27 step D from methyl 2-(tert-butoxy)-2-(6-methyl-7-oxo-4-(p-tolyl)-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate and 3,4-methylenedioxybenzyl chloride (50% in dcm), and was isolated as beige solid after reverse phase chromatography (41%): 1H NMR (400 MHz, CHLOROFORM-d) ppm 0.99 (s, 9H), 2.42 (s, 3H), 3.67 (s, 3H), 5.46 (s, 1H), 5.63-5.81 (m, 2H), 5.92 (s, 2H), 6.01 (d, J=2.9 Hz, 1H), 6.70-6.84 (m, 3H), 7.00 (d, J=2.8 Hz, 1H), 7.27-7.30 (m, 2H), 7.30-7.38 (m, 1H), 7.46-7.58 (m, 1H). LCMS (m/z) ES+=503 (M+1).

Workup

  1. customwas isolated as beige solid after reverse phase chromatography (41%)

Sources & evidence

ORD record
ord-42a2eeefd8de44959a9194be6b970920
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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