Dichloromethane → Hydrochloric Acid

HRID 1180045Notes

Reaction equation

HRID 1180045 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH2:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][C:45](=[O:54])[N:46]([CH3:53])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:40][CH:39]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:63]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:35][CH2:36][CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][C:45](=[O:54])[N:46]([CH3:53])[C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)=[CH:42][CH:43]=3)=[O:14])=[CH:15][CH:16]=2)[CH2:6][CH2:7]1.[ClH:63]

Participants

8

Reactant 6

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 7365324-(4-Methylpiperazin-1-yl)benzoic acidHCID 69520583Methyl-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl Ester

Product 2

HCID 313Hydrochloric AcidHCID 69519700HCID 69519700, compound

Procedure

A solution of 4-(4-methylpiperazino)benzoic acid (0.3 mmol), EDAC (0.36 mmol) and triethylamine (1.0 mmol) in CH2Cl2 (10 mL) was added N-hydroxybenzoetriazole and N-methyl-N-phenyl-carbamic acid 4-(2-amino-ethyl)phenyl ester as its TFA salt (0.3 mmol). The mixture was stirred 16 h at rt and purified by preparative HPLC (Gilson) to give the title compound in 54% yield as its crystalline hydrochloride after treatment with HCl in diethyl ether.

Workup

  1. custompurified by preparative HPLC (Gilson)

Sources & evidence

ORD record
ord-b29b6e3bfecf4a91bfdae17ebd039ca6
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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