Water → (S)-1-{9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-2-ethyl-butan-1-one

HRID 507169Notes

Reaction equation

HRID 507169 reaction equation
N1C=CC=CC=1.[CH2:7]([CH:9]([CH2:13][CH3:14])[C:10](Cl)=[O:11])[CH3:8].[F:15][C:16]([F:50])([F:49])[C:17]1[CH:18]=[C:19]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:20][N:21]([C@@H:28]1[C:34]2=[CH:35][C:36]3[CH2:37][O:38][CH2:39][C:40]=3[CH:41]=[C:33]2[NH:32][CH2:31][CH2:30][CH2:29]1)[C:22]1[N:23]=[N:24][N:25]([CH3:27])[N:26]=1.O>ClCCl>[F:50][C:16]([F:15])([F:49])[C:17]1[CH:18]=[C:19]([CH:42]=[C:43]([C:45]([F:46])([F:47])[F:48])[CH:44]=1)[CH2:20][N:21]([C:22]1[N:23]=[N:24][N:25]([CH3:27])[N:26]=1)[C@@H:28]1[C:34]2=[CH:35][C:36]3[CH2:37][O:38][CH2:39][C:40]=3[CH:41]=[C:33]2[N:32]([C:10](=[O:11])[CH:9]([CH2:13][CH3:14])[CH2:7][CH3:8])[CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 759542-Ethylbutyryl chlorideHCID 59432492(S)-(3,5-bis-trifluoromethyl-benzyl)-(3,5,6,7,8,9-hexahydro-1H-2-oxa-5-aza-cyclohepta[f]inden-9-yl)-(2-methyl-2H-tetrazol-5-yl)-amine

Product 1

HCID 59432529(S)-1-{9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-2-ethyl-butan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add pyridine (0.35 mmol) followed by 2-ethyl-butyryl chloride (0.35 mmol) to a solution of (S)-(3,5-Bis-trifluoromethyl-benzyl)-(3,5,6,7,8,9-hexahydro-1H-2-oxa-5-aza-cyclohepta[f]inden-9-yl)-(2-methyl-2H-tetrazol-5-yl)-amine (Example 73, Step 7) (0.17 mmol) in dichloromethane (3 mL). After stirring at room temperature for 14 h, dilute the reaction with dichloromethane (10 mL) followed by water (10 mL). Separate the organic phase and wash the aqueous with dichloromethane (2×10 mL). Dry the combined organics over sodium sulfate, filter, and remove solvent in vacuo. Chromatograph the crude product over silica gel using ethyl acetate/hexane (10-50%) to elute to obtain the title compound as a colorless foam. MS (ES+): 611 (M+H).

Workup

  1. additiondilute
  2. customSeparate the organic phase
  3. washwash the aqueous with dichloromethane (2×10 mL)
  4. dry with materialDry the combined organics over sodium sulfate
  5. filtrationfilter
  6. customremove solvent in vacuo
  7. washto elute

Sources & evidence

ORD record
ord-ee089f7834c040f7bbb8c54e2c4245e6
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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