Isopropyl iodide → HCID 68563587, compound
Reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([N:22]4[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]4)=[O:21])=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:6]1)[CH:2](C)C.[CH3:31]OC(C1C=C2C(C(C3OCCNC3)=CN2)=CC=1)=O.IC(C)C.COC(C1C=C2C(C(C3OCCN(C(C)C)C3)=CN2)=CC=1)=O.N1(C(N)=O)CCNCC1.O[Li].O.CC(N1CCNCC1)C>>[CH:1]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([N:22]4[CH2:27][CH2:26][N:25]([CH:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]4)=[O:21])=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:6]1)([CH3:31])[CH3:2]Participants
Procedure
According to the procedure described for the synthesis of [3-(4-isobutyl-morpholin-2-yl)-1H-indol-6-yl]-(4-isopropyl-piperazin-1-yl)-methanone (example 90) the title compounds was synthesized in consecutive steps from 3-morpholin-2-yl-1H-indole-6-carboxylic acid methyl ester and 2-iodopropane (commercially available) leading to 3-(4-isopropyl-morpholin-2-yl)-1H-indole-6-carboxylic acid methyl ester (MS (m/e): 303.4 (MH+)) which was converted to the title compounds according to the procedure described for the conversion of an ester functionality to a piperazine amide functionality like in example 72, step 2. The title compound was prepared from 3-(4-isopropyl-morpholin-2-yl)-1H-indole-6-carboxylic acid methyl ester and (after ester cleavage with LiOH.H2O), 1-(2-propyl)-piperazine (commercially available). The title compound was obtained as light yellow foam. MS (m/e): 399.3 (MH+).
Sources & evidence
- ORD record
- ord-9f30314e2e4a4f748e69b3187c27210a
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514433B2
Reaction notes
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