Allylamine → HCID 19088441, compound

HRID 1463910Notes

Reaction equation

HRID 1463910 reaction equation
O.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:15]2[CH:16]=[C:17]([CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36](/[CH:40]=[CH:41]/[C:42]5[S:43][CH:44]=[C:45]([CH:47]6[CH2:50][CH2:49][CH2:48]6)[N:46]=5)[CH:35]=4)=[O:32])=[C:25]([CH:29]=3)[C:26](O)=[O:27])[S:18][C:14]=2[N:13]2[C:51]([CH3:54])=[N:52][N:53]=[C:12]2[CH2:11][N:10]=1.Cl.C(N=C=[N:60][CH2:61][CH2:62][CH2:63]N(C)C)C.C(N)C=C>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:15]2[CH:16]=[C:17]([CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([CH2:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36](/[CH:40]=[CH:41]/[C:42]5[S:43][CH:44]=[C:45]([CH:47]6[CH2:48][CH2:49][CH2:50]6)[N:46]=5)[CH:35]=4)=[O:32])=[C:25]([C:26]([NH:60][CH2:61][CH:62]=[CH2:63])=[O:27])[CH:29]=3)[S:18][C:14]=2[N:13]2[C:51]([CH3:54])=[N:52][N:53]=[C:12]2[CH2:11][N:10]=1

Participants

5

Reactant 3

HCID 7853AllylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67809643HCID 67809643, compound

Product 1

HCID 19088441HCID 19088441, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.1 g (0.13 mmol) of (E)-5-[2-[4-(2-chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]ethyl]-2-[2-[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]phenylamino]-2-oxoethyl]-benzoic acid monohydrate, 0.03 g (0.16 mmol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride, 0.02 mL (4 mmol) of allylamine and 15 mL of dry CH2Cl2 was stirred at room temperature under nitrogen for 18 hours and concentrated to dryness. The residue was purified by thick layer chromatography using ethyl acetate/CH3OH (5:1) as the eluent. The product was isolated and partitioned between CH2Cl2 and dilute NH4OH. The organic phases were concentrated and the residue triturated with hot ethyl acetate and filtered. The filtrates were concentrated and the solid triturated with diethyl ether and filtered to give 60 mg (57%) of (E)-4-[ 2-[4-(2-Chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1,4]-diazepin-2-yl]ethyl]-N-[3-[2-(4-cyclobutyl-2-thiazolyl)ethenyl]-phenyl]-2-[(2-propenylamino)carbonyl]benzeneacetamide as a tan powder: mp 127°-132° C.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by thick layer chromatography
  3. customThe product was isolated
  4. custompartitioned between CH2Cl2 and dilute NH4OH
  5. concentrationThe organic phases were concentrated
  6. customthe residue triturated with hot ethyl acetate
  7. filtrationfiltered
  8. concentrationThe filtrates were concentrated
  9. customthe solid triturated with diethyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-42adc9a74a274a2da3b0a6c319c578bd
Source dataset
uspto-grants-1994_04
Patent number
US05302590

Reaction notes

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