Diisopropylamine → HCID 145857670, compound

HRID 2216107Notes

Reaction equation

HRID 2216107 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]([C:10]1[S:11][C:12]([S:28][CH3:29])=[C:13]([S:15]([C:18]2[CH:26]=[C:25]([Br:27])[C:21]3[N:22]=[CH:23][NH:24][C:20]=3[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[CH:36][C:33]=1[CH2:34]Br.C(NC(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]([C:10]1[S:11][C:12]([S:28][CH3:29])=[C:13]([S:15]([C:18]2[CH:26]=[C:25]([Br:27])[C:21]3[N:22]([CH2:34][C:33]4[CH:36]=[CH:37][C:38]([N+:40]([O-:42])=[O:41])=[CH:39][C:32]=4[F:31])[CH:23]=[N:24][C:20]=3[CH:19]=2)(=[O:16])=[O:17])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]([C:10]1[S:11][C:12]([S:28][CH3:29])=[C:13]([S:15]([C:18]2[CH:26]=[C:25]([Br:27])[C:21]3[N:22]=[CH:23][N:24]([CH2:34][C:33]4[CH:36]=[CH:37][C:38]([N+:40]([O-:42])=[O:41])=[CH:39][C:32]=4[F:31])[C:20]=3[CH:19]=2)(=[O:16])=[O:17])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzeneHCID 145857605HCID 145857605, compound

Product 2

HCID 145857607HCID 145857607, compoundHCID 145857670HCID 145857670, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution of {[4-(7-bromo-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 187–188: step c) 0.097 g, 0.183 mmol) in DMF (3 mL) was treated with 2-fluoro-4-nitrobenzylbromide (0.064 g, 0.274 mmol) and diisopropylamine (0.051 mL, 0.365 mmol) and heated to 40° C. 24 h. The solution was diluted with EtOAc and washed well with water (4×35 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to afford the products ({4-[7-bromo-1-(2-fluoro-4-nitro-benzyl)-1H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophen-2-yl)-imino-methyl)-carbamic acid tert-butyl ester and ({4-[7-bromo-3-(2-fluoro-4-nitro-benzyl)-3H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophen-2-yl)-imino-methyl)-carbamic acid tert-butyl ester (0.012 g, 10%) as a brown solid. C25H23BrFN5O6S3: 684.00 (M+1) found 684.50.

Workup

  1. custom24 h
  2. washwashed well with water (4×35 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5aef2305f9ea4a89a5742bec7afbd238
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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