Triethylamine hydrochloride → HCID 178421833, compound

HRID 507178Notes

Reaction equation

HRID 507178 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[CH2:6][N:7]([C:33]1[N:34]=[N:35][N:36]([CH3:38])[N:37]=1)[C@H:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[C:10]2[CH:24]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:26]([CH3:28])=[CH:27][C:9]1=2.[N-:48]=[N+:49]=[N-:50].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:43][C:42]([F:45])([F:44])[C:40]1[CH:39]=[C:5]([CH:4]=[C:3]([C:2]([F:46])([F:1])[F:47])[CH:41]=1)[CH2:6][N:7]([C:33]1[N:34]=[N:35][N:36]([CH3:38])[N:37]=1)[C@H:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]3[NH:50][N:49]=[N:48][N:21]=3)=[CH:18][CH:17]=2)[C:10]2[CH:24]=[C:25]([C:29]([F:30])([F:31])[F:32])[C:26]([CH3:28])=[CH:27][C:9]1=2

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 59432441HCID 59432441, compound

Product 1

HCID 178421833HCID 178421833, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Heat a mixture of (S)-4-{5-[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl}-benzonitrile (Example 192) (0.13 g, 0.19 mmol), sodium azide (0.04 g, 0.60 mmol) and triethylamine hydrochloride (0.08 g, 0.60 mmol) in anhydrous toluene (5 mL) at 110° C. under nitrogen for 20 h. Dilute the cooled mixture with ethyl acetate (50 mL) and wash with aqueous 0.1N HCl (10 mL) and brine (10 mL). Dry over anhydrous sodium sulfate. Filter and remove the solvent under reduced pressure. Purify the residue by column chromatography on silica gel, eluting with MeOH/EtOAc (0-20%), to provide the title compound (0.12 g, 82%). MS (ES+): 711 (M+H).

Workup

  1. temperatureHeat
  2. washwash with aqueous 0.1N HCl (10 mL) and brine (10 mL)
  3. dry with materialDry over anhydrous sodium sulfate
  4. filtrationFilter
  5. customremove the solvent under reduced pressure
  6. customPurify the residue by column chromatography on silica gel
  7. washeluting with MeOH/EtOAc (0-20%)

Sources & evidence

ORD record
ord-27e28ecc5dd3480e94a46404e73e04c9
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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