Cesium carbonate → HCID 59432510, compound

HRID 507135Notes

Reaction equation

HRID 507135 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([C:24]1[N:25]=[N:26][N:27]([CH3:29])[N:28]=1)[C@H:8]1[CH2:14][CH2:13][CH2:12][NH:11][C:10]2[CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:17]([CH3:19])=[CH:18][C:9]1=2.Br[CH2:40][C:41]#[N:42].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.C(OCC)(=O)C>[F:38][C:2]([F:37])([F:1])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:32]=1)[CH2:6][N:7]([C:24]1[N:25]=[N:26][N:27]([CH3:29])[N:28]=1)[C@H:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:40][C:41]#[N:42])[C:10]2[CH:15]=[C:16]([C:20]([F:21])([F:22])[F:23])[C:17]([CH3:19])=[CH:18][C:9]1=2

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 59432408(S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amine

Product 1

HCID 59432510HCID 59432510, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-amine (Example 3, Step 18) (0.09 mmol) in dimethylformamide (3 mL), add bromoacetonitrile (0.36 mmol) and cesium carbonate (0.36 mmol). After stirring the reaction at 60° C. for 6 h, cool to room temperature and dilute with water (20 mL) and ethyl acetate (30 mL). Separate the organic phase and wash the aqueous with ethyl acetate (2×10 mL). Dry the combined organics over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-40%), to afford the title compound as a colorless foam. MS (ES+): 592 (M+H).

Workup

  1. customthe reaction at 60° C. for 6 h
  2. customSeparate the organic phase
  3. washwash the aqueous with ethyl acetate (2×10 mL)
  4. dry with materialDry the combined organics over sodium sulfate
  5. filtrationfilter
  6. customremove solvent under vacuum
  7. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-40%)

Sources & evidence

ORD record
ord-3b012f5a1c1e45b08c9fbc37c4d8ffb5
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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