Ammonium Chloride → HCID 178442494, compound

HRID 1055098Notes

Reaction equation

HRID 1055098 reaction equation
[F:1][C:2]1[C:3]([NH:18][CH:19]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:20][C:21]([NH2:24])=[N:22][OH:23])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1.[C:29](C1NC=CN=1)(C1NC=CN=1)=[O:30].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>C1COCC1.ClCCl>[F:1][C:2]1[C:3]([NH:18][CH:19]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:20][C:21]2[NH:22][O:23][C:29](=[O:30])[N:24]=2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86714766HCID 86714766, compound2×

Product 1

HCID 178442494HCID 178442494, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic 3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]-N′-hydroxy-4,4-dimethyl-pentanamidine, 125a, (0.034 g, 0.087 mmol) and carbonyl diimidazole (0.014 g, 0.087 mmol) in THF (1 mL) was added N,N-diisopropylethylamine (0.045 mL, 0.260 mmol). The reaction mixture was stirred at room temperature for 48 hours. Aqueous ammonium chloride and dichloromethane were added and the layers were separated with a phase separator. The residue was purified on a C18 column (acetonitrile/0.1% formic acid) to afford the final product: 1H NMR (400 MHz, Acetone) δ 11.23 (s, 1H), 8.54 (dd, J=9.8, 2.8 Hz, 1H), 8.36 (s, 1H), 8.20 (s, 1H), 8.13 (d, J=3.7 Hz, 1H), 6.81 (s, 1H), 5.00 (d, J=11.2 Hz, 1H), 3.15 (d, J=14.8 Hz, 3H), 2.94 (dd, J=14.4, 11.9 Hz, 2H), 1.16 (s, 8H); LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=1.58 minutes (M+H) 390.06.

Workup

  1. customthe layers were separated with a phase separator
  2. customThe residue was purified on a C18 column (acetonitrile/0.1% formic acid)

Sources & evidence

ORD record
ord-aea6d0ea71014df0b6442073071649a2
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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