Diisopropylethylamine → [2-({2-[2-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indol-6-ylcarbamoyl]-1H-indole-5-carbonyl}-amino)-ethyl]-carbamic acid tert-butyl ester

HRID 724519Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([NH2:22])[CH:16]=2)=[O:12])([CH3:4])([CH3:3])[CH3:2].FC1C([O:31][C:32]([C:34]2[NH:35][C:36]3[C:41]([CH:42]=2)=[CH:40][C:39]([C:43](=[O:55])[NH:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[CH:38][CH:37]=3)=O)=C(F)C(F)=C(F)C=1F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:51]([O:50][C:48](=[O:49])[NH:47][CH2:46][CH2:45][NH:44][C:43]([C:39]1[CH:40]=[C:41]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:32](=[O:31])[NH:22][C:17]1[CH:16]=[C:15]3[C:20]([CH:21]=[C:13]([C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:23])[NH:14]3)=[CH:19][CH:18]=1)=[CH:42]2)=[O:55])([CH3:54])([CH3:52])[CH3:53]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of above amine 36 and compound 33 (0.226 g, 0.44 mmol) in dry DMF (6 ml) in the presence of DIEA (77 μl, 0.44 mmol) was stirred at 55° C. for 2 days. After removal of solvent, the residue was recrystalized from MeOH-ether to give compound 37 in a quantitative yield.

Workup

customAfter removal of solvent
customthe residue was recrystalized from MeOH-ether

Sources & evidence

ORD record: ord-ec84d62f70c04121a1d14d281c95c94a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141680B2

Reaction notes

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