Toluene → HCID 54204444, compound

HRID 1737278Notes

Reaction equation

[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11][C@@H:10]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31](C)[CH:30]=2)=[O:27])[C:9]1=[O:36])=[O:6])([CH3:4])([CH3:3])[CH3:2].[N-:37]=[C:38]=[O:39].[C:40]1(C)C=CC=CC=1>>[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11][C@@H:10]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:37]([CH:38]=[O:39])[CH3:40])[CH:30]=2)=[O:27])[C:9]1=[O:36])=[O:6])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 3

HCID 1140Toluene

HCID 105034Isocyanate

HCID 10322988HCID 10322988, compound

Product 1

HCID 54204444HCID 54204444, compoundYield 65%

Procedure

The resolved aminobenzodiazepine of Example 26 (980 mg, 2.8 mmol) in toluene (10 ml) was treated with the isocyanate prepared from the acid of Example 56B (985 mg, 5.5 mmol) following the method of Example 38. The product was purified by flash chromatography on silica gel (eluant EtOAc:hexane fr 75;25 v/v) to provide the title compound (960 mg, 65%).

Workup

customThe product was purified by flash chromatography on silica gel (eluant EtOAc:hexane fr 75;25 v/v)

Sources & evidence

ORD record: ord-e169822247584bb39bcf4cd001d90625
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05962451

Reaction notes

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