Allylamine → HCID 66748238, compound

HRID 2401775Notes

Reaction equation

HRID 2401775 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[S:10][C:11]=2[C:12](O)=[O:13])=[CH:4][CH:3]=1.C1C=[CH:25][C:26]2N(O)N=[N:29][C:27]=2C=1.CCN=C=NCCCN(C)C.C(N)C=C>C(Cl)Cl>[CH2:27]([NH:29][C:12]([C:11]1[S:10][C:9]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[N:8][C:7]=1[CH2:6][C:5]1[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:13])[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 7853AllylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66748269HCID 66748269, compound

Product 1

HCID 66748238HCID 66748238, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazole-5-carboxylic acid (220 mg, 0.665 mmol) in DCM (4.05 mL) was added HOBT (98.8 mg, 0.732 mmol) and EDCI (204 mg, 1.06 mmol) at room temperature and the mixture was stirred for 30 min. To the solution was added 2-propen-1-amine (0.200 mL, 2.66 mmol) then the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM (10 mL) and washed with water (3 mL) and brine (2 mL), then dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→75/25) to give 150 mg of the title compound as a yellow solid (61% yield). LC/MS (FA) ES+ 370. 1H NMR (400 MHz, CDCl3) δ: 8.74-8.72 (m, 2H), 7.79-7.77 (m, 2H), 7.35-7.32 (m, 2H), 7.27-7.25 (m, 2H), 5.94-5.80 (m+bs, 2H), 5.25-5.20 (m, 2H), 4.48 (s, 2H), 4.06-4.02 (m, 2H).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washwashed with water (3 mL) and brine (2 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→75/25)

Sources & evidence

ORD record
ord-172bff563728459bb49752ced59b7b30
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

Loading…