Dimethylformamide → HCID 51355043, compound

HRID 707863Notes

Reaction equation

HRID 707863 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:22]=[CH:21][C:9]3[C:10]4[N:11]=[C:12]([C:18]([OH:20])=O)[S:13][C:14]=4[CH2:15][CH2:16][O:17][C:8]=3[CH:7]=2)[CH:3]=[N:2]1.CN(C)C=O.C(NC(C)C)(C)C.[CH:35]([NH:38][CH2:39][CH2:40][OH:41])([CH3:37])[CH3:36]>>[OH:41][CH2:40][CH2:39][N:38]([CH:35]([CH3:37])[CH3:36])[C:18]([C:12]1[S:13][C:14]2[CH2:15][CH2:16][O:17][C:8]3[CH:7]=[C:6]([C:4]4[CH:3]=[N:2][NH:1][CH:5]=4)[CH:22]=[CH:21][C:9]=3[C:10]=2[N:11]=1)=[O:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 79942-(Isopropylamino)ethanolHCID 582038838-(1H-Pyrazol-4-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid

Product 1

HCID 51355043HCID 51355043, compoundYield 15.1%

Conditions

Temperature
50 °C

Procedure

To a solution of 8-(1H-Pyrazol-4-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (363.8 mg, 1.161 mmol) in N,N-dimethylformamide (39-60 equiv.) and N,N-Diisopropylamine (1.5 equiv.) was added 2-(isopropylamino)ethanol (133.1 mg, 1.29 mmol) followed by the addition of N,N,N′N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uranium hexafluorophosphate (1.1 equiv.). The reaction mixture was heated at 50° C. for 2 hrs to 24 hours depending on when complete by LCMS. Reaction mixture was concentrated on the genevac and purified by HPLC or diluted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated in vacuo prior to purification by HPLC to give 103 (70 mg, 15% yield, M+1 399.1)

Workup

  1. customReaction mixture
  2. concentrationwas concentrated on the genevac
  3. custompurified by HPLC
  4. additiondiluted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto purification by HPLC

Sources & evidence

ORD record
ord-da52de70fbec43838392016202262104
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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