Phosgene → HCID 59432299, compound

HRID 507137Notes

Reaction equation

HRID 507137 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.[C:39](Cl)([Cl:41])=[O:40].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[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]([C:39]([Cl:41])=[O:40])[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

6

Reactant 4

HCID 6371PhosgeneHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 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 59432299HCID 59432299, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

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) (0.91 mmol) in toluene (5 mL), add phosgene (0.91 mmol) as a 1.93 M solution in toluene. Next, add diisopropylethylamine (0.96 mmol) dropwise at room temperature. After stirring at room temperature for 1 h, dilute the reaction with ethyl acetate (10 mL) and wash with water (5 mL). Dry the organic phase over sodium sulfate, filter, and remove solvent under a stream of nitrogen. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-25%), to afford the title compound as a colorless foam. MS (ES+): 615 (M+H).

Workup

  1. additiondilute
  2. washwash with water (5 mL)
  3. dry with materialDry the organic phase over sodium sulfate
  4. filtrationfilter
  5. customremove solvent under a stream of nitrogen
  6. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-25%)

Sources & evidence

ORD record
ord-950923dda4fd436fbb06d4bebfa633f1
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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