Triethylamine → HCID 86629650, compound

HRID 911418Notes

Reaction equation

HRID 911418 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[S:4].[C:7]([C:9]1[CH:25]=[CH:24][C:12]2[CH2:13][CH2:14][N:15]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:16][CH2:17][C:11]=2[C:10]=1[OH:26])#[N:8].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.O1CCOCC1.CCOC(C)=O>[C:7]([C:9]1[CH:25]=[CH:24][C:12]2[CH2:13][CH2:14][N:15]([C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])[CH2:16][CH2:17][C:11]=2[C:10]=1[O:26][C:3](=[S:4])[N:2]([CH3:6])[CH3:1])#[N:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 86661653HCID 86661653, compound

Product 1

HCID 86629650HCID 86629650, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Add dimethylthiocarbamoyl chloride (197 mg, 1.58 mmol) to a stirred solution of 7-cyano-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (150 mg, 0.53 mmol), DMAP (6 mg, 0.05 mmol) and dry triethylamine (300 μL) in dry 1,4-dioxane (5 mL) under an atmosphere of nitrogen and heat at 120° C. for 6 h. Cool and continue stirring for 2 days at ambient temperature. Dilute with EtOAc, wash with 1N aqueous HCl, water, saturated aqueous Na2CO3 and brine. Dry over MgSO4 then concentrate in vacuo. Purify by chromatography on silica gel eluting with EtOAc:heptane (0:1 to 3:10) to give the desired intermediate as a white solid (158 mg, 81%).

Workup

  1. temperatureCool
  2. washwash with 1N aqueous HCl, water, saturated aqueous Na2CO3 and brine
  3. dry with materialDry over MgSO4
  4. concentrationthen concentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with EtOAc:heptane (0:1 to 3:10)

Sources & evidence

ORD record
ord-096fe6484f0044c6a10ee97b97c57e5a
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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