Water → HCID 90313400, compound

HRID 1523983Notes

Reaction equation

HRID 1523983 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH2:22][C:23]([O:25]C)=[O:24])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.O[Li].O.O>C1COCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:12][C:13]=2[F:14])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 90313085HCID 90313085, compound

Product 1

HCID 90313400HCID 90313400, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-yloxy)acetate (50 mg, 0.14 mmol) in THF (2 mL) were added LiOH.H2O (63 mg, 1.5 mmol) and H2O (2 mL). The mixture was stirred at rt for 14 hours. The THF was removed under reduced pressure, and the residue diluted with 15 mL of water, washed with DCM (5 mL×2), and then acidified with 1 N HCl to pH=7. The precipitate was collected and washed with water and dried under high vacuum to give the title compound (40 mg, 95% yield). MS (ESI): mass calcd. for C18H14FN3O3, 339.10; m/z found, 340.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 13.02 (s, 1H), 8.36 (s, 1H), 8.01 (s, 1H), 7.88 (m, 1H), 7.55 (d, J=13.0, 1H), 7.48 (d, J=9.2, 1H), 7.40 (d, J=7.4, 1H), 7.33 (m, 1H), 7.08-7.00 (m, 2H), 6.69 (s, 2H), 4.76 (s, 2H).

Workup

  1. customThe THF was removed under reduced pressure
  2. additionthe residue diluted with 15 mL of water
  3. washwashed with DCM (5 mL×2)
  4. customThe precipitate was collected
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-1044a596810f4e60bb93508c9c99587c
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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