Dimethylamine → HCID 15952368, compound

HRID 2244257Notes

Reaction equation

HRID 2244257 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]([C:11]2[N:20]3[C:14]([CH2:15][N:16]([C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[CH2:39][C:40](O)=[O:41])=[CH:29][CH:28]=4)=[O:26])[C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19]3)=[CH:13][CH:12]=2)=[O:10])[CH:2]=1.CNC.[CH2:46]([NH:48][CH2:49][CH3:50])[CH3:47]>>[CH2:46]([N:48]([CH2:49][CH3:50])[C:40](=[O:41])[CH2:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:30]1[CH:31]=[CH:32][C:27]([C:25]([N:16]2[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH2:19][N:20]3[C:11]([C:9]([NH:8][CH2:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:10])=[CH:12][CH:13]=[C:14]3[CH2:15]2)=[O:26])=[CH:28][CH:29]=1)[CH3:47]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8021DiethylamineHCID 68686684HCID 68686684, compound

Product 1

HCID 15952368HCID 15952368, compoundYield 60%

Procedure

The title compound was prepared in essentially the same manner as Example 68, replacing 4′-{[3-{[(pyridin-3-ylmethyl)amino]carbonyl}-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]carbonyl}-1,1′-biphenyl-2-carboxylic acid with (4′-{[3-{[(pyridin-3-ylmethyl)amino]carbonyl}-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl]carbonyl}-1,1′-biphenyl-2-yl)acetic acid of Example 35, and dimethylamine with diethylamine. Purification by flash chromatography using a solvent gradient of 1 to 4% methanol in dichloromethane gave the title compound (0.158 g, 60%) as an off-white solid.

Workup

  1. customThe title compound was prepared in essentially the same manner as Example 68
  2. customPurification by flash chromatography

Sources & evidence

ORD record
ord-60225ba4a7e14a5ca4ae9564c7e29036
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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