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Water → HCID 67314181, compound

HRID 1012782
Notes
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Reaction equation

HRID 1012782 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[O:15][C:14]([C:17]([NH:19][C@@H:20]4[CH:25]5[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]5)[CH2:21]4)=[O:18])=[CH:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:28][S:29]([Cl:32])(=[O:31])=[O:30].C(N(CC)CC)C.O>C1COCC1.CN(C=O)C>[ClH:32].[N:22]12[CH2:23][CH2:24][CH:25]([CH2:26][CH2:27]1)[C@@H:20]([NH:19][C:17]([C:14]1[O:15][C:16]3[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])[CH:3]=4)=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]=1)=[O:18])[CH2:21]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58675161HCID 58675161, compound

Product 1

HCID 67314181HCID 67314181, compound

Reagents, catalysts & solvents 1

HCID 21974620
tetrahydrofuran N,N-dimethylformamide
Solvent

Procedure

73 mg (0.20 mmol) of 7-(3-aminophenyl)-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide (Example 114), 69 mg (0.61 mmol) of methanesulphonyl chloride and 0.14 ml (1.01 mmol) of triethylamine are heated in 3 ml of THF/DMF (1:1) at 50° C. overnight. Cooling is followed by addition of water, filtration and removal of the solvent under reduced pressure. Purification takes place by preparative HPLC. The product is dissolved in methanol, and an excess of 1N hydrochloric acid is added. The solvent is removed under reduced pressure. Drying under high vacuum results in 16 mg (14% of theory) of the title compound.

Workup

  1. temperatureCooling
  2. customPurification
  3. dissolutionThe product is dissolved in methanol
  4. additionan excess of 1N hydrochloric acid is added
  5. customThe solvent is removed under reduced pressure
  6. customDrying under high vacuum

Sources & evidence

ORD record
ord-c4349f1f9ba4492ea4db584001924c77
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977485B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes