Methyl 1-amino-5-carbamoyl-1H-pyrrole-3-carboxylate → Methyl 2-(3-(acetoxylmethyl)phenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

HRID 63788Notes

Reaction equation

HRID 63788 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=O)[CH:7]=1)(=[O:3])[CH3:2].[NH2:14][N:15]1[C:19]([C:20](=[O:22])[NH2:21])=[CH:18][C:17]([C:23]([O:25][CH3:26])=[O:24])=[CH:16]1>>[O:4]([CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[NH:21][C:20](=[O:22])[C:19]3=[CH:18][C:17]([C:23]([O:25][CH3:26])=[O:24])=[CH:16][N:15]3[N:14]=2)[CH:9]=[CH:10][CH:11]=1)[C:1]([CH3:2])=[O:3]

Participants

3

Reactant 2

HCID 66985220Methyl 1-amino-5-carbamoyl-1H-pyrrole-3-carboxylateHCID 856670533-Formylbenzyl acetate

Product 1

HCID 137010729Methyl 2-(3-(acetoxylmethyl)phenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-carboxylateYield 39%

Procedure

According to the general preparation methods described in example 5 above, 3-formylbenzyl acetate reacts with compound 3 to give compound IIIb as offwhite solid in 39.0% yield. m.p. 202-203° C. 1H NMR (300 MHz, DMSO-d6): δ 12.29 (s, 1H), 8.19 (d, J=1.7 Hz, 1H), 7.96 (s, 1H), 7.92 (dt, J=1.7, 7.2 Hz, 1H), 7.58-7.53 (m, 2H), 7.24 (d, J=1.7 Hz, 1H), 5.16 (s, 2H), 3.81 (s, 3H), 2.10 (s, 3H). LC-MS: 342 (M+1).

Workup

  1. customAccording to the general preparation methods
  2. customto give compound IIIb as offwhite solid in 39.0% yield

Sources & evidence

ORD record
ord-c00c26f466ae445ba134a7f9f1b4be24
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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