N,N-Dimethyl-1,3-propanediamine → HCID 22238168, compound

HRID 2415721Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[C:11]([F:21])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[NH:24][C:25](=[O:36])[C:26]1[CH:31]=[C:30](Cl)[CH:29]=[CH:28][C:27]=1[N+:33]([O-:35])=[O:34].[CH3:37][N:38]([CH3:43])[CH2:39][CH2:40][CH2:41][NH2:42]>>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[C:11]([F:21])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[NH:24][C:25](=[O:36])[C:26]1[CH:31]=[C:30]([NH:42][CH2:41][CH2:40][CH2:39][N:38]([CH3:43])[CH3:37])[CH:29]=[CH:28][C:27]=1[N+:33]([O-:35])=[O:34]

Participants

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamine

HCID 22238178HCID 22238178, compound

Product 1

HCID 22238168HCID 22238168, compoundYield 76%

Procedure

Using an analogous procedure to that described in the second paragraph of the portion of Example 23 which is concerned with the preparation of starting materials, 4-chloro-3-(5-chloro-2-nitrobenzamido)-N-(3-fluoro-5-morpholinophenyl)benzamide was reacted with 3-dimethylaminopropylamine to give the title compound in 76% yield; NMR Spectrum: (DMSOd6) 1.62-1.74 (m, 2H), 2.12 (s, 6H), 2.27 (t, 2H), 3.08-3.13 (m, 4), 3.18-3.22 (m, 2H), 3.69-3.74 (m, 4H), 6.58 (d, 1H), 6.67 (m, 2H), 7.15-7.2 (m, 2H), 7.42 (t, 1H), 7.69 (d, 1H), 7.68 (d, 1H), 7.82 (d, 1H), 8.04 (d, 1H), 8.26 (s, 1H), 10.32 (s, 111); Mass Spectrum: M+H+ 599.

Sources & evidence

ORD record: ord-80ed81101ac64386a7a579e6f5d40699
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821965B1

Reaction notes

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