(2,4-Dimethoxy-benzylamino)-acetic acid → 4-(2,4-Dimethoxy-benzyl)-7-isopropyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

HRID 351836Notes

Reaction equation

[CH:1]([C:4]1[CH:15]=[CH:14][C:7]2[NH:8][C:9](=[O:13])O[C:11](=[O:12])[C:6]=2[CH:5]=1)([CH3:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:19]=1[CH2:20][NH:21][CH2:22]C(O)=O>CC1C=CC(C)=CC=1>[CH3:16][O:17][C:18]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:19]=1[CH2:20][N:21]1[C:11](=[O:12])[C:6]2[CH:5]=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:15]=[CH:14][C:7]=2[NH:8][C:9](=[O:13])[CH2:22]1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 6-isopropyl-1H-benzo[d][1,3]oxazine-2,4-dione (3.0 g, 15 mmol) containing (2,4-dimethoxy-benzylamino)-acetic acid (3.7 g, 16 mmol) in p-xylene (40 mL) was heated under reflux (150° C.) for 2.5 h. After cooling to room temperature the precipitate was filtered off and washed with p-xylene (2×20 ml). Yield: 4.9 g (90%). m/z 367 (M—H−).

Workup

temperaturewas heated
temperatureAfter cooling to room temperature the precipitate
filtrationwas filtered off
washwashed with p-xylene (2×20 ml)

Sources & evidence

ORD record: ord-a598e07e831b4753a5cf0cf85705debf
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743789B2

Reaction notes

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