Dimethylformamide → HCID 58284034, compound

HRID 628095Notes

Reaction equation

HRID 628095 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:8][CH2:9][CH2:10][C:11]3[CH:17]=[C:16]([C:18]4[N:22]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=5[F:30])[N:21]=[CH:20][N:19]=4)[S:15][C:12]=3[C:13]=2[N:14]=1)([OH:3])=O.[CH3:31][N:32]([CH3:35])[CH:33]=O.[CH:36]([N:39](CC)[CH:40](C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[N:22]1[C:18]([C:16]2[S:15][C:12]3[C:13]4[N:14]=[C:4]([C:1]([N:39]5[CH2:40][CH2:33][N:32]([CH3:35])[CH2:31][CH2:36]5)=[O:3])[CH:5]=[CH:6][C:7]=4[O:8][CH2:9][CH2:10][C:11]=3[CH:17]=2)=[N:19][CH:20]=[N:21]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57900197HCID 57900197, compound

Product 1

HCID 58284034HCID 58284034, compoundYield 32%

Procedure

5-(2-Carboxy-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole (0.052 g, 0.12 mmol) was dissolved in N,N-dimethylformamide (0.904 mL, 0.0117 mol) and treated sequentially with N,N-diisopropylethylamine (0.127 mL, 0.732 mmol) 1-methyl-piperazine, (0.0541 mL, 0.488 mmol), then N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (HATU, 0.0556 g, 0.146 mmol). The reaction was stirred at room temperature overnight. Saturated sodium bicarbonate was added and extracted with ethyl acetate. Organics were dried over sodium sulfate and concentrated. The crude product was submitted HPLC purification to give 433 (32% yield). MS: (ESI+)=509.3

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialOrganics were dried over sodium sulfate
  3. concentrationconcentrated
  4. customHPLC purification

Sources & evidence

ORD record
ord-0ddeb3a8a919491a9feb630f71fd698f
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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