5-Bromo-3-indoleacetic acid → N-[2-(5-Bromo-1H-indol-3-yl)-acetyl]-N'-[3-chloro-4-(4-methyl-piperazin-1-yl)-benzyl]-guanidine

HRID 1819705Notes

Reaction equation

HRID 1819705 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]([NH2:26])=[N:11][C:12](=[O:25])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20](OC)[CH:21]=3)[NH:16][CH:15]=2)[CH:5]=[C:4]([Cl:27])[C:3]=1[NH:28][C:29](=O)[CH3:30].[Br:32]C1C=C2C(=CC=1)NC=C2CC(O)=O.Cl[C:47]1C=C(CN)C=C[C:52]=1[N:53]1[CH2:58]CN(C)CC1>>[Br:32][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:13][C:12]([NH:11][C:10]([NH:9][CH2:8][C:6]1[CH:7]=[CH:2][C:3]([N:28]2[CH2:47][CH2:52][N:53]([CH3:58])[CH2:30][CH2:29]2)=[C:4]([Cl:27])[CH:5]=1)=[NH:26])=[O:25]

Participants

4

Reactant 3

HCID 967345-Bromo-3-indoleacetic acidHCID 57887239(3-Chloro-4-(4-methylpiperazin-1-yl)phenyl)methanamineHCID 178488081HCID 178488081, compound

Product 1

HCID 178480667N-[2-(5-Bromo-1H-indol-3-yl)-acetyl]-N'-[3-chloro-4-(4-methyl-piperazin-1-yl)-benzyl]-guanidine

Procedure

In a manner similar to that used in the preparation of the compound of example 2, but using 2-(5-bromo-1H-indol-3-yl)acetic acid in step 19 (A) and (3-chloro-4-(4-methylpiperazin-1-yl)phenyl)methanamine (preparation F) in step 19 (B), the title compound was prepared. MS (ESI) (M+H)+=517.02/518.98 1H-NMR (500 MHz, CD3OD) δ 7.73 (s, 1 H), 7.45 (s, 1 H), 7.27-7.38 (m, 3 H), 7.17-7.26 (m, 2 H), 4.49 (s, 2 H), 3.93 (s, 2 H), 3.57-3.68 (m, 2 H), 3.47-3.58 (m, 2 H), 3.28-3.40 (m, 2 H), 3.06-3.18 (m, 2 H), 2.96-3.01 (s, 3 H).

Sources & evidence

ORD record
ord-e9a6ef7feb21409c886a652e8976f2a4
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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