Methanol → HCID 66597677, compound

HRID 40955Notes

Reaction equation

HRID 40955 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:14]([N:18]3[CH:22]=[C:21]([C:23]4[C:24]5[CH:31]=[CH:30][N:29](COCC[Si](C)(C)C)[C:25]=5[N:26]=[CH:27][N:28]=4)[CH:20]=[N:19]3)[CH2:15][C:16]#[N:17])[CH:11]=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44].CO.C(N)CN>>[F:46][C:45]([F:48])([F:47])[C:43]([OH:49])=[O:44].[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:14]([N:18]3[CH:22]=[C:21]([C:23]4[C:24]5[CH:31]=[CH:30][NH:29][C:25]=5[N:26]=[CH:27][N:28]=4)[CH:20]=[N:19]3)[CH2:15][C:16]#[N:17])[CH:11]=[N:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 3301EthylenediamineHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57477895HCID 57477895, compound

Product 1

HCID 66597677HCID 66597677, compoundYield 58.07%

Procedure

The 3-[5-(phenylthio)pyridin-3-yl]-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.110 g, 0.000199 mol) was dissolved in DCM (5.0 mL, 0.078 mol) and TFA (2.0 mL, 0.026 mol), and the mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo, and the resulting residue was dissolved in methanol (5.0 mL, 0.12 mol), and ethylenediamine (0.1 mL, 0.002 mol) was added. This reaction mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo, and the crude product was purified by LCMS (pH=2) to yield the title compound as an amorphous solid (62 mg, 58.07%). 1H NMR (400 MHz, DMSO): δ □12.80 (s), 9.10 (s) 8.87 (d), 8.60 (s), 8.50 (s), 8.43 (s), 7.82 (s), 7.78 (m), 7.39 (m), 7.25 (m), 7.18 (d), 6.20 (m), 3.84 (m), 3.70 (m). LC/MS (M+H)F: m/z=424.15

Workup

  1. customThe solvent was removed in vacuo
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe crude product was purified by LCMS (pH=2)

Sources & evidence

ORD record
ord-9e2327d061d747c39679069f83fe9ea2
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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