Lithium hydroxide, monohydrate → HCID 59828881, compound

HRID 1191158Notes

Reaction equation

HRID 1191158 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:22]=[N:23][C:24]([S:27]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])=[O:28])=[CH:25][CH:26]=1.O.[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[NH:19][CH2:20][C:21]1[CH:22]=[N:23][C:24]([S:27]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86624191HCID 86624191, compound

Product 1

HCID 59828881HCID 59828881, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 7-chloro-6-{[6-(2,2-dimethylpropane-sulfonyl)-pyridin-3-yl-methyl]-amino}-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (142 mg, 0.27 mmol) in methanol (5 mL). Add lithium hydroxide hydrate (23 mg, 0.54 mmol) and stir for 1 h. Mix with silica gel (1 g), concentrate in vacuo, and purify by chromatography on silica gel (12 g) eluting with DCM/(chloroform:methanol:concentrated NH4OH) (1:0 to 9:1 gradient) to give 7-chloro-6-{[6-(2,2-dimethylpropane-sulfonyl)-pyridin-3-yl-methyl]-amino}-2,3,4,5-tetrahydro-1H-benzo[d]azepine (91 mg, 78%). MS (APCI) m/z: 422 (M+H)+.

Workup

  1. additionMix with silica gel (1 g)
  2. concentrationconcentrate in vacuo
  3. custompurify by chromatography on silica gel (12 g)
  4. washeluting with DCM/(chloroform:methanol:concentrated NH4OH) (1:0 to 9:1 gradient)

Sources & evidence

ORD record
ord-a03926a3cd654dccab10cc0e6a0a3274
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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