2-(Aminomethyl)-1H-indole methanesulphonate → HCID 25096698, compound

HRID 2067671Notes

Reaction equation

HRID 2067671 reaction equation
CC1C=C(N2CCN(CCOC3C=CC=CC=3)C2=O)SC=1C(O)=O.[F:25][C:26]1[CH:47]=[CH:46][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:40][C:39]([C:41]([OH:43])=O)=[C:38]([CH3:44])[CH:37]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.CS(O)(=O)=O.[NH:53]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:55]=[C:54]1[CH2:62][NH2:63]>>[NH:53]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:55]=[C:54]1[CH2:62][NH:63][C:41]([C:39]1[S:40][C:36]([N:33]2[CH2:34][CH2:35][N:31]([CH2:30][C:29]3[CH:28]=[CH:27][C:26]([F:25])=[CH:47][CH:46]=3)[C:32]2=[O:45])=[CH:37][C:38]=1[CH3:44])=[O:43]

Participants

4

Reactant 3

HCID 441196302-(Aminomethyl)-1H-indole methanesulphonateHCID 580314563-Methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acidHCID 580314655-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 25096698HCID 25096698, compoundYield 75%

Procedure

Following the procedures as described in Example 55, making variations as required to replace 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with (1H-indol-2-yl)methanamine methanesulfonate, the title compound was obtained as an off-white solid in 75% yield: 1H NMR (300 MHz, CDCl3) δ 9.18 (br s, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.30-7.22 (m, 2H), 7.19-6.98 (m, 4H), 6.36 (s, 1H), 6.28 (t, J=5.9 Hz, 1H), 6.10 (s, 1H), 4.62 (d, J=5.9 Hz, 2H), 4.42 (s, 2H), 3.81-3.73 (m, 2H), 3.45-3.38 (m, 2H), 2.50 (s, 3H); MS (ES+) m/z 463.2 (M+1), 485.2 (M+23).

Sources & evidence

ORD record
ord-63b7d7c432ab4713b64f5f456cee09f3
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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