HCID 59784178, compound → HCID 178462494, compound

HRID 470300Notes

Reaction equation

HRID 470300 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([O:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:19][C:20]1[CH:21]=[C:22]([CH:45]=[CH:46][C:47]=1[NH2:48])[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][N:34]2[CH2:38][CH2:37][C:36]3([CH2:42][CH2:41][N:40]([CH2:43][CH3:44])[CH2:39]3)[CH2:35]2)=[CH:28][CH:27]=1)=[O:24]>CC(N(C)C)=O>[CH2:43]([N:40]1[CH2:41][CH2:42][C:36]2([CH2:35][N:34]([CH2:33][CH2:32][C:29]3[CH:30]=[CH:31][C:26]([NH:25][C:23]([C:22]4[CH:45]=[CH:46][C:47]5[NH:48][C:4]([C:3]6[CH:6]=[C:7]([C:10]7[C:11]([O:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=7)[CH:8]=[CH:9][C:2]=6[OH:1])=[N:19][C:20]=5[CH:21]=4)=[O:24])=[CH:27][CH:28]=3)[CH2:38][CH2:37]2)[CH2:39]1)[CH3:44].[CH2:43]([N:40]1[CH2:41][CH2:42][C:36]2([CH2:35][N:34]([CH2:33][CH2:32][C:29]3[CH:30]=[CH:31][C:26]([NH:25][C:23]([C:22]4[CH:45]=[CH:46][C:47]5[NH:48][C:4]([C:3]6[CH:6]=[C:7]([C:10]7[C:11]([OH:16])=[N:12][CH:13]=[CH:14][CH:15]=7)[CH:8]=[CH:9][C:2]=6[OH:1])=[N:19][C:20]=5[CH:21]=4)=[O:24])=[CH:27][CH:28]=3)[CH2:38][CH2:37]2)[CH2:39]1)[CH3:44]

Participants

5

Reactant 2

HCID 59784178HCID 59784178, compoundHCID 670585753,4-Diamino-N-{4-[2-(7-ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-benzamide HCl salt

Product 2

HCID 178462494HCID 178462494, compoundHCID 178462495HCID 178462495, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-benzaldehyde (20 mg) and 3,4-Diamino-N-{4-[2-(7-ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-benzamide HCl salt (60 mg) in dimethylacetamide (1.5 ml) was heated at 95° C. for 3 h then cooled and purified by RP-HPLC (0.1% TFA) to afford (A) 2-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-1H-benzoimidazole-5-carboxylic acid {4-[2-(7-ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-amide (10 mg) LCMS MH+ 617.5 as well as (B) 2-[2-Hydroxy-5-(2-hydroxy-pyridin-3-yl)-phenyl]-1H-benzoimidazole-5-carboxylic acid {4-[2-(7-ethyl-2,7-diaza-spiro[4.4]non-2-yl)-ethyl]-phenyl}-amide (10 mg) LCMS MH+ 603.7.

Workup

  1. temperaturethen cooled
  2. custompurified by RP-HPLC (0.1% TFA)

Sources & evidence

ORD record
ord-d96d8b06427f4799a6c7b669fc2fe6f8
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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