Water → HCID 178521352, compound

HRID 1893274Notes

Reaction equation

HRID 1893274 reaction equation
[Si]([N:5]=[N+:6]=[N-:7])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:26]([C:28]1[CH:29]=[C:30]([C:34]2([OH:61])[CH2:39][CH2:38][CH:37]([N:40]3[CH2:43][CH:42]([NH:44][C:45]([CH2:47][NH:48][C:49](=[O:60])[C:50]4[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=4)=[O:46])[CH2:41]3)[CH2:36][CH2:35]2)[CH:31]=[CH:32][CH:33]=1)#[N:27].O>C1COCC1.C(OCC)(=O)C.N.CO>[OH:61][C:34]1([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([C:26]3[NH:27][N:7]=[N:6][N:5]=3)[CH:29]=2)[CH2:39][CH2:38][CH:37]([N:40]2[CH2:41][CH:42]([NH:44][C:45]([CH2:47][NH:48][C:49](=[O:60])[C:50]3[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:58])([F:59])[F:57])[CH:51]=3)=[O:46])[CH2:43]2)[CH2:36][CH2:35]1

Participants

9

Reactant 4

HCID 962WaterHCID 78378AzidotrimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 49764701HCID 49764701, compound

Product 1

HCID 178521352HCID 178521352, compound

Reagents, catalysts & solvents 4

HCID 222AmmoniaSolvent2×HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

TMSN3 (Fluka, 50 mg, 0.42 mmol), TBAF (Aldrich, 1.0 N in THF, 0.5 mL, 0.5 mmol) and N-({1-[4-(3-cyano-phenyl)-4-hydroxy-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (as prepared in Example 48, less polar isomer, 70 mg, 0.14 mmol) were dissolved in THF (2 mL) and water (0.5 mL) mixed solvent. The reaction mixture was subjected to microwave irradiation at 120° C. for 20 min. The crude reaction mixture was loaded on a silica gel column using a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customirradiation at 120° C. for 20 min
  2. customThe crude reaction mixture

Sources & evidence

ORD record
ord-26cc443ac0f946e68be5467cd55cdd9e
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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