Dimethylformamide → HCID 66559172, compound

HRID 1530593Notes

Reaction equation

HRID 1530593 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[C:19]([C:22]([OH:24])=O)[N:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:25]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].CN(C)C=O.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[C:64]([N:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1)([CH3:67])([CH3:66])[CH3:65]>>[C:64]([N:68]1[CH2:73][CH2:72][N:71]([C:22]([C:19]2[N:20]=[CH:21][C:16]3[O:15][CH2:14][CH2:13][N:12]4[CH:25]=[C:9]([C:8]5[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][N:7]=5)[N:10]=[C:11]4[C:17]=3[CH:18]=2)=[O:24])[CH2:70][CH2:69]1)([CH3:67])([CH3:66])[CH3:65]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 35305721-Tert-butylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68312737HCID 68312737, compound

Product 1

HCID 66559172HCID 66559172, compound

Procedure

[2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine-10-carboxylic acid (0.140 g, 0.411 mmol) was dissolved in N,N-Dimethylformamide (3.18 mL, 0.0411 mol) at room temperature. N,N-Diisopropylethylamine (0.287 mL, 0.00164 mol) was added followed by N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (0.172 g, 0.452 mmol). The suspension was stirred for 10 minutes. 1-tert-butylpiperazine (0.0878 g, 0.617 mmol) was added and the reaction mixture was stirred for 1 hour. LCMS shows complete conversion to product. The reaction mixture was concentrated to dryness and was purified by reversed phase HPLC to give 203. 1H NMR (400 MHz, DMSO) δ 8.42 (s, 1H), 8.39 (s, 1H), 8.14 (s, 1H), 8.09 (s, 1H), 7.94 (s, 1H), 7.94 (s, 1H), 5.76 (dt, J=13.2, 6.6 Hz, 1H), 4.64 (s, 4H), 3.56 (br d, J=48.6 Hz, 8H), 1.49 (d, J=6.6 Hz, 6H), 1.02 (s, 9H). LCMS 465.3.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customwas purified by reversed phase HPLC

Sources & evidence

ORD record
ord-2453831b38784506a6b2b1867492a5a3
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…