Toluene → HCID 23152320, compound

HRID 1012322Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][C:13](=O)[C:14]([NH:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]2C(C3CCCCC3)=[C:31]3[N:25]([CH2:26][CH2:27][O:28][C:29]4[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:30]=43)[C:24]=2[CH:45]=1)=[O:19])([CH3:16])[CH3:15].[C:47]1([CH3:53])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(O)(=O)C>[CH:47]1([C:53]2[C:23]3[CH:22]=[CH:21][C:20]([C:18]([NH:17][C:14]([C:13]4[NH:12][C:3]5[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=5[N:1]=4)([CH3:16])[CH3:15])=[O:19])=[CH:45][C:24]=3[N:25]3[C:31]=2[C:30]2[CH:39]=[CH:40][C:41]([O:43][CH3:44])=[CH:42][C:29]=2[O:28][CH2:27][CH2:26]3)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 4-amino-3-{2-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-2-methylpropionylamino}benzoate (0.73 g, 1.16 mmol) was dissolved in acetic acid (14.0 ml), and the mixture was stirred at 100° C. for 2 hr. The mixture was allowed to cool to room temperature, toluene was added, and the solvent was evaporated under reduced pressure. To the obtained residue were added methanol and water. The precipitate was collected by filtration, washed with water, and dried in vacuo to give methyl 2-{1-[(12-cyclohexyl-3-methoxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carbonyl)amino]-1-methylethyl}-3H-benzimidazole-5-carboxylate (0.67 g, yield 95%).

Workup

temperatureto cool to room temperature
customthe solvent was evaporated under reduced pressure
additionTo the obtained residue were added methanol and water
filtrationThe precipitate was collected by filtration
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-a6de8cd128ee4647bcbae5f78a5769f6
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977331B1

Reaction notes

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