Dimethylformamide → HCID 58203832, compound

HRID 1849333Notes

Reaction equation

HRID 1849333 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[CH:8][N:7]=[C:6]2[C:10]2[S:11][C:12]3[CH2:13][CH2:14][O:15][C:16]4[CH:23]=[C:22]([C:24]5[CH:25]=[N:26][N:27]([CH2:29][C:30]([CH3:33])([OH:32])[CH3:31])[CH:28]=5)[CH:21]=[CH:20][C:17]=4[C:18]=3[N:19]=2)[CH2:2]1.CN(C)[CH:36]=[O:37].[CH:39](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>>[OH:32][C:30]([CH3:33])([CH3:31])[CH2:29][N:27]1[CH:28]=[C:24]([C:22]2[CH:21]=[CH:20][C:17]3[C:18]4[N:19]=[C:10]([C:6]5[N:5]([CH:3]6[CH2:4][N:1]([C:36](=[O:37])[CH3:39])[CH2:2]6)[CH:9]=[CH:8][N:7]=5)[S:11][C:12]=4[CH2:13][CH2:14][O:15][C:16]=3[CH:23]=2)[CH:25]=[N:26]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58203765HCID 58203765, compound

Product 1

HCID 58203832HCID 58203832, compound

Procedure

Compound 411 (0.110 g, 0.000238 mol) dissolved in N,N-Dimethylformamide (3.72 mL, 0.0480 mol) and treated sequentially with N,N-Diisopropylethylamine (0.248 mL, 0.00143 mol) Acetic acid (0.0270 mL, 0.000476 mol) then N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (0.108 g, 0.000285 mol). Stir at r.t. overnight. Add sat. sodium bicarbonate, extract with ethyl acetate. Dried combined organics over sodium sulfate and concentrated. The crude product was purified by rHPLC to give 416. MS: (ESI+)=505.2. 1H NMR (400 MHz, DMSO) δ 8.37 (d, J=8.3 Hz, 1H), 8.15 (s, 1H), 7.95-7.90 (m, 2H), 7.43 (dd, J=8.3, 1.8 Hz, 1H), 7.28 (d, J=1.8 Hz, 1H), 7.17 (d, J=1.1 Hz, 1H), 6.24-6.13 (m, 1H), 4.78-4.66 (m, 2H), 4.51-4.39 (m, 2H), 4.36 (t, J=5.5 Hz, 2H), 4.04 (s, 2H), 3.39 (t, J=5.1 Hz, 2H), 1.84 (s, 3H), 1.10 (s, 6H).

Workup

  1. extractionAdd sat. sodium bicarbonate, extract with ethyl acetate
  2. customDried
  3. concentrationconcentrated
  4. customThe crude product was purified by rHPLC

Sources & evidence

ORD record
ord-65e84008e06841bb908d0be598d5e948
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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