Diisopropylethylamine → (S)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-N1-[2-(4-methyl-piperazin-1-ylsulphonylamino)-ethyl]-2-morpholin-4-ylsulphonylamino-succinamide acetate

HRID 744902Notes

Reaction equation

HRID 744902 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]([CH:33]1[CH2:35][CH2:34]1)[C:6](=[O:32])[C@@H:7]([NH:22][S:23]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)(=[O:25])=[O:24])[CH2:8][C:9]([NH:11][CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([NH2:21])=[NH:20])[CH2:14]1)=[O:10].[CH3:36][N:37]1[CH2:42][CH2:41][N:40]([S:43](Cl)(=[O:45])=[O:44])[CH2:39][CH2:38]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:30]([OH:44])(=[O:29])[CH3:31].[NH2:20][C:19](=[NH:21])[N:15]1[CH2:16][CH2:17][CH2:18][C@@H:13]([CH2:12][NH:11][C:9](=[O:10])[CH2:8][C@H:7]([NH:22][S:23]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)(=[O:25])=[O:24])[C:6]([N:5]([CH:33]2[CH2:35][CH2:34]2)[CH2:4][CH2:3][NH:2][S:43]([N:40]2[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]2)(=[O:45])=[O:44])=[O:32])[CH2:14]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 111716174-methylpiperazine-1-sulfonyl ChlorideHCID 67746050(S)-N1-(2-amino-ethyl)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-2-morpholin-4-ylsulphonylamino-succinamide hydrochloride

Product 1

HCID 67746342(S)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-N1-[2-(4-methyl-piperazin-1-ylsulphonylamino)-ethyl]-2-morpholin-4-ylsulphonylamino-succinamide acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

330 mg of (S)-N1-(2-amino-ethyl)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-2-morpholin-4-ylsulphonylamino-succinamide hydrochloride are stirred at room temperature for 20 hours together with 162 mg of 4-methyl-piperazin-1-ylsulphonyl chloride and 0.49 ml of Hunig's base in 8 ml of methylene chloride. The reaction mixture is chromatographed over silica gel with ethyl acetate/acetone/glacial acetic acid/water 2:2:2:1. 14.9.1 mg of pure crystalline (S)-N4-[(S)-1-(amino-imino-methyl)-piperidin-3-ylmethyl]-N1-cyclopropyl-N1-[2-(4-methyl-piperazin-1-ylsulphonylamino)-ethyl]-2-morpholin-4-ylsulphonylamino-succinamide acetate (1:2), MS (ISP): 665.6 (M+H) and 333.7 (M+2H), are obtained.

Workup

  1. customThe reaction mixture is chromatographed over silica gel with ethyl acetate/acetone/glacial acetic acid/water 2:2:2:1

Sources & evidence

ORD record
ord-db8ce89af9394756961bf5a9cd99d33d
Source dataset
uspto-grants-1996_09
Patent number
US05559232

Reaction notes

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