Diisopropylethylamine → HCID 54015629, compound

HRID 974334Notes

Reaction equation

HRID 974334 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[CH:11][CH2:12]O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(C(C)C)C(C)C)C.[NH2:23][C:24]1[S:25][C:26]2[CH2:27][CH2:28][NH:29][CH2:30][CH2:31][C:32]=2[N:33]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[NH2:23][C:24]1[S:25][C:26]2[CH2:27][CH2:28][N:29]([CH2:12][CH:11]=[CH:10][C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[NH:1][CH:2]=[CH:3]4)[CH2:30][CH2:31][C:32]=2[N:33]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 199857852-Amino-4,5,6,7,8-pentahydrothiazolo[5,4-d]azepineHCID 53697942HCID 53697942, compound

Product 1

HCID 54015629HCID 54015629, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

At -15° C., a solution of 63 mg (0.55 mmol) of methanesulphochloride in 6 ml of chloroform is added dropwise to a stirred solution of 95 mg (0.55 mmol) of 3-(5-indolyl)allyl alcohol and 142 mg (1.10 mmol) of N-ethyl-N,N-diisopropylamine in 6 ml of anhydrous methylene chloride and the resulting mixture is stirred for 15 hours at -5° C. It is evaporated down in vacuo at 20° C., the evaporation residue is dissolved in 3 ml of anhydrous dimethylformamide, 370 mg (2.20 mmol) of 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine are added and the mixture is stirred for 4 hours at 50° C. and for 3 hours at 70° C. The mixture is then evaporated down in vacuo, distributed between chloroform and water and the dried and filtered chloroform solution is evaporated down in vacuo. The evaporation residue is purified by triple column chromatography on neutral aluminium oxide (toluene/ethyl acetate/ethanol=4:1:0.5). Yield: 8 mg (4.5% of theory), Melting point: 60°-65° C. (foamy). Molecular peak (m/z) Calculated: 324 Found: 324

Workup

  1. customIt is evaporated down in vacuo at 20° C.
  2. dissolutionthe evaporation residue is dissolved in 3 ml of anhydrous dimethylformamide
  3. stirringthe mixture is stirred for 4 hours at 50° C. and for 3 hours at 70° C
  4. customThe mixture is then evaporated down in vacuo
  5. customthe dried
  6. filtrationfiltered chloroform solution
  7. customis evaporated down in vacuo
  8. customThe evaporation residue is purified by triple column chromatography on neutral aluminium oxide (toluene/ethyl acetate/ethanol=4:1:0.5)

Sources & evidence

ORD record
ord-771b56d196bd406a94301c86c4f5dd16
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Reaction notes

Loading…