Lithium Hydroxide → HCID 86712684, compound

HRID 1779036Notes

Reaction equation

HRID 1779036 reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[N:27]=[C:26]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH2:36][C:37]([O:39]C)=[O:38])[C:25]([C:41]([F:44])([F:43])[F:42])=[CH:24][N:23]=2)=[CH:17][CH:16]=1)[CH2:11][CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CO.O>[C:3]([O:7][C:8]([N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[N:27]=[C:26]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH2:36][C:37]([OH:39])=[O:38])[C:25]([C:41]([F:43])([F:44])[F:42])=[CH:24][N:23]=2)=[CH:17][CH:16]=1)[CH2:11][CH2:12][OH:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86712683HCID 86712683, compound

Product 1

HCID 86712684HCID 86712684, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (143 mg, 5.98 mmol) was added to a solution of methyl 2-(2-(2-(2-((4-(((tert-butoxycarbonyl)(2-hydroxyethyl)amino)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate (A73) (0.440 g, 0.748 mmol) in THF (10 mL), MeOH (1 mL) and water (1 mL) and the resulting mixture stirred at room temperature for 20 hours. Additional LiOH (107 mg, 4.48 mmol) was added and the mixture heated to 40° C. for 24 hours. The volatiles were removed in vacuo. The residue was diluted with a 10% citric acid solution (20 mL) and 1 M HCl (0.5 mL) until pH 3 was obtained. The resulting precipitate was collected by filtration and dried to give the title compound A74 as a pale yellow solid (0.421 g, 98%); 1H NMR (300 MHz, d6-DMSO) δ 10.21 (s, 1H), 8.67 (s, 1H), 7.71 (d, J=8.0 Hz, 2H), 7.24-7.17 (m, 6H), 4.38 (brs, 2H), 3.64 (brs, 2H), 3.47-3.03 (m, 8H), 1.42 (s, 9H). LCMS-B: rt 7.786 min; m/z 575 [M+H]+.

Workup

  1. temperaturethe mixture heated to 40° C. for 24 hours
  2. customThe volatiles were removed in vacuo
  3. additionThe residue was diluted with a 10% citric acid solution (20 mL) and 1 M HCl (0.5 mL) until pH 3
  4. customwas obtained
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-f2ef8d6b88b0402e91ab3be63ce546ba
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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