Dimethylformamide → HCID 59362808, compound

HRID 1625479Notes

Reaction equation

HRID 1625479 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[F:37])[CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([NH:14][CH:15]([C:19]2[S:20][C:21]([C:24]3[C:32]4[C:27](=[N:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)=[CH:22][CH:23]=2)[C:16]([OH:18])=O)=[O:13])[C:7]1=[O:33].C[N:39](C)C=O.[Cl-].[NH4+].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:16]([CH:15]([NH:14][C:12]([C:8]1[C:7](=[O:33])[N:6]([CH2:5][C:4]2[CH:34]=[CH:35][C:36]([F:37])=[C:2]([F:1])[CH:3]=2)[CH:11]=[CH:10][CH:9]=1)=[O:13])[C:19]1[S:20][C:21]([C:24]2[C:32]3[C:27](=[N:28][CH:29]=[CH:30][CH:31]=3)[NH:26][CH:25]=2)=[CH:22][CH:23]=1)(=[O:18])[NH2:39]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24861063HCID 24861063, compound

Product 1

HCID 59362808HCID 59362808, compound

Procedure

{[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-[5-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiophen-2-yl]-acetic acid (0.039 g, 0.000075 mol;) was dissolved in N,N-Dimethylformamide (3 g, 0.04 mol;) and Ammonium chloride (0.010 g, 0.00019 mol;), N,N-Diisopropylethylamine (65.2 uL, 0.000374 mol;), and N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium Hexafluorophosphate (0.037 g, 0.000097 mol;) were added. After 2 hours the reaction was found to be complete by LC-MS 1.18 520.03. The crude reaction was directly injected onto the Gilson for purification to give the pure product. ES (+) MS m/e=520.03; NMR (400 MHz, DMSO-d6) δ ppm 5.22 (m, 2H), 5.83 (d, 1H, J=8 Hz), 6.60 (t, 1H, J=8 Hz), 7.07 (d, 1H, J=4 Hz), 7.14-7.21 (m, 2H), 7.23 (d, 1H, J=8 Hz) 7.38-7.49 (m, 3H), 7.81 (m, 1H), 8.19-8.30 (m, 3H), 8.37 (dd. 1H), 10.53 (d, 1H), 11.95 (s, 1H)

Workup

  1. customThe crude reaction
  2. customwas directly injected onto the Gilson for purification
  3. customto give the pure product

Sources & evidence

ORD record
ord-86c7534b8cc04786a3d670e5b79a3198
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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