1,4,5,6-Tetrahydropyrimidin-2-amine → (2S)-2-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-benzenesulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid tert-butyl ester

HRID 427318Notes

Reaction equation

HRID 427318 reaction equation
CO[C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](=[O:37])(=[O:36])[NH:11][C@H:12]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:13][NH:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](OC)=[O:25])=[CH:18][CH:17]=1.[NH2:39][C:40]1[NH:41][CH2:42][CH2:43][CH2:44][N:45]=1>CN(C)C=O>[C:32]([O:31][C:29](=[O:30])[C@@H:12]([NH:11][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3](=[O:38])[NH:39][C:40]1[NH:45][CH2:44][CH2:43][CH2:42][N:41]=1)(=[O:37])=[O:36])[CH2:13][NH:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](=[O:25])[NH:39][C:40]2[NH:45][CH2:44][CH2:43][CH2:42][N:41]=2)=[CH:18][CH:17]=1)([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 570397222-((1S)-1-tert-Butoxycarbonyl-2-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-ethylsulfamoyl)-benzoic acid methyl ester

Product 1

HCID 56996588(2S)-2-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-benzenesulfonylamino)-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-benzoylamino)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

75 mg (0.13 mmol) of 2-((1S)-1-tert-butoxycarbonyl-2-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-ethylsulfamoyl)-benzoic acid methyl ester was dissolved in 1 ml of dimethylformamide and 68 mg (0.69 mmol) of 2-amino-1,4,5,6-tetrahydropyrimidine was added. The reaction was stirred at room temperature for 20 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel eluting with dichloromethane/methanol (1/1), followed by dichloromethane/methanol/acetic acid/water (85/15/1.5/1.5). Yield 54 mg. MS (ES+): m/e=683.3 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica gel eluting with dichloromethane/methanol (1/1)

Sources & evidence

ORD record
ord-9d9cd502988b47cab74c3e568786fb9b
Source dataset
uspto-grants-2001_11
Patent number
US06313119B1

Reaction notes

Loading…