Water → HCID 11549451, compound

HRID 507128Notes

Reaction equation

HRID 507128 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[CH2:6][N:7]([C@H:14]1[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:16]2[CH:28]=[C:29]([C:33]([F:36])([F:35])[F:34])[C:30]([CH3:32])=[CH:31][C:15]1=2)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH2:46]([O:48][C:49](=[O:52])[CH2:50]Br)[CH3:47].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH2:46]([O:48][C:49](=[O:52])[CH2:50][N:25]1[CH2:24][CH2:23][CH:22]([CH2:21][N:17]2[CH2:18][CH2:19][CH2:20][C@H:14]([N:7]([CH2:6][C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:44])[F:45])[CH:39]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:37]=3)[C:8]3[N:9]=[N:10][N:11]([CH3:13])[N:12]=3)[C:15]3[CH:31]=[C:30]([CH3:32])[C:29]([C:33]([F:34])([F:35])[F:36])=[CH:28][C:16]2=3)[CH2:27][CH2:26]1)[CH3:47]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 11541960HCID 11541960, compound

Product 1

HCID 11549451HCID 11549451, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (S)-(3,5-Bis-trifluoromethyl-benzyl)-(7-methyl-1-piperidin-4-ylmethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)-amine (Example 120) (0.18 mmol) in DMF (3 mL), add bromo-acetic acid ethyl ester (0.54 mmol) and cesium carbonate (0.90 mmol). After heating the mixture at 50° C. for 30 minutes, cool to room temperature and dilute the reaction with water (15 mL) and extract with ethyl acetate (3×10 mL). Dry the combined organic phases over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-50%), to give the title compound as a colorless foam. MS (ES+): 736 (M+H).

Workup

  1. temperaturecool to room temperature
  2. additiondilute
  3. extractionextract with ethyl acetate (3×10 mL)
  4. dry with materialDry the combined organic phases over sodium sulfate
  5. filtrationfilter
  6. customremove solvent under vacuum
  7. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-50%)

Sources & evidence

ORD record
ord-1a7f07b53c9d4773b605aae036278865
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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