Dimethylformamide → HCID 67050557, compound

HRID 1190318Notes

Reaction equation

HRID 1190318 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@@H:2]1[CH2:3][OH:4].C(NC(C)C)(C)C.CN(C)C=O.[Br:20][C:21]1[CH:37]=[CH:36][C:24]2[C:25]3[N:26]=[C:27]([C:33](Cl)=[O:34])[S:28][C:29]=3[CH2:30][CH2:31][O:32][C:23]=2[CH:22]=1>C(OCC)(=O)C>[Br:20][C:21]1[CH:37]=[CH:36][C:24]2[C:25]3[N:26]=[C:27]([C:33]([N:1]4[CH2:7][CH2:6][CH2:5][C@@H:2]4[CH2:3][OH:4])=[O:34])[S:28][C:29]=3[CH2:30][CH2:31][O:32][C:23]=2[CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 2724541Prolinol, (R)-HCID 86652318HCID 86652318, compound

Product 1

HCID 67050557HCID 67050557, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of D-(−)-Prolinol (0.205 g, 2.03 mmol) in N,N-Diisopropylamine (0.758 mL, 4.35 mmol) and N,N-Dimethylformamide (4.49 mL, 58.0 mmol) at room temperature was added 8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carbonyl chloride (0.500 g, 1.45 mmol) portionwise. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with brine, and concentrated in vacuo to give (8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-((R)-2-hydroxymethyl-pyrrolidin-1-yl)-methanone which was not further purified.

Workup

  1. washwashed with brine
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7be7f817bda4499fa91591479f8d5143
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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