1,5-Naphthalenedisulfonic acid → 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-{(R)-1-(3,4-diethyl-benzyl)-2-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-amide naphthalene-1,5-disulphonate

HRID 1869603Notes

Reaction equation

HRID 1869603 reaction equation
[C:1]1([S:15]([OH:18])(=[O:17])=[O:16])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([OH:14])(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:19]([C:21]1[CH:22]=[C:23]([CH:62]=[CH:63][C:64]=1[CH2:65][CH3:66])[CH2:24][C@@H:25]([NH:41][C:42]([N:44]1[CH2:49][CH2:48][CH:47]([N:50]2[CH2:56][CH2:55][C:54]3[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=3[NH:52][C:51]2=[O:61])[CH2:46][CH2:45]1)=[O:43])[C:26]([N:28]1[CH2:33][CH2:32][N:31]([CH:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)[CH2:30][CH2:29]1)=[O:27])[CH3:20]>C(O)(C)C>[CH2:19]([C:21]1[CH:22]=[C:23]([CH:62]=[CH:63][C:64]=1[CH2:65][CH3:66])[CH2:24][C@@H:25]([NH:41][C:42]([N:44]1[CH2:49][CH2:48][CH:47]([N:50]2[CH2:56][CH2:55][C:54]3[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=3[NH:52][C:51]2=[O:61])[CH2:46][CH2:45]1)=[O:43])[C:26]([N:28]1[CH2:29][CH2:30][N:31]([CH:34]2[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]2)[CH2:32][CH2:33]1)=[O:27])[CH3:20].[C:1]1([S:15]([O-:18])(=[O:17])=[O:16])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([O-:14])(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 66661,5-Naphthalenedisulfonic acidHCID 100322974-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-{(R)-1-(3,4-diethyl-benzyl)-2-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-amide

Product 1

HCID 866195614-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-{(R)-1-(3,4-diethyl-benzyl)-2-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-amide naphthalene-1,5-disulphonate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.427 g naphthalene-1,5-disulphonic acid (4.95 mmol) in 70 ml isopropanol is added to 3.25 g (4.94 mmol) 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-{(R)-1-(3,4-diethyl-benzyl)-2-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-amide and heated to 80° C. The now clear solution is cooled to ambient temperature, by lowering the temperature of the heating bath by 5° C. every 6 hours. The resultant suspension is filtered, the isolated solid is dried for 12 hours at 40° C.

Workup

  1. temperatureThe now clear solution is cooled to ambient temperature
  2. customby 5° C.
  3. customevery 6 hours
  4. filtrationThe resultant suspension is filtered
  5. customthe isolated solid is dried for 12 hours at 40° C.

Sources & evidence

ORD record
ord-9a8d9bb5322344e7ba3930312ccc068a
Source dataset
uspto-grants-2009_12
Patent number
US07638625B2

Reaction notes

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