Diisopropylamine → HCID 145857700, compound

HRID 723151Notes

Reaction equation

HRID 723151 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]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[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]=[C:37]([N+:40]([O-:42])=[O:41])[CH:38]=[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]=[C:37]([N+:40]([O-:42])=[O:41])[CH:38]=[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 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzeneHCID 145857605HCID 145857605, compound

Product 2

HCID 140043488HCID 140043488, compoundHCID 145857700HCID 145857700, compoundYield 17.7%

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 ((from above step c) 0.132 g, 0.248 mmol) in dry DMF (3 mL) was treated with 2-fluoro-5-nitrobenzylbromide (0.087 g, 0.373 mmol) and diisopropylamine (0.070 mL, 0.497 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-5-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-5-nitro-benzyl)-3H-benzoimidazole-5-sulfonyl]-5-methylsulfanyl-thiophen-2-yl}-imino-methyl)-carbamic acid tert-butyl ester (0.015 g, 9%) as a brown solid. C25H23BrFN5O6S3: 684.00 (M+1) found 684.60.

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-1836755674674f6a934b3f7afa72b8d1
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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