Water → HCID 178457292, compound

HRID 2406151Notes

Reaction equation

HRID 2406151 reaction equation
[CH2:1]([N:4]([CH2:47][CH2:48][CH3:49])[C:5]([CH2:7][O:8][C:9](=[O:46])[CH2:10][CH2:11][NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([N:24]2[CH2:45][CH2:44][C:27]3([NH:31]/[C:30](=[N:32]/[C:33]([C:35]4[C:40]([NH2:41])=[N:39][C:38]([NH2:42])=[C:37]([Cl:43])[N:36]=4)=[O:34])/[NH:29][CH2:28]3)[CH2:26][CH2:25]2)=[O:23])[CH:17]=1)(=[O:15])=[O:14])=[O:6])[CH2:2][CH3:3].O.[C:51]([OH:58])(=[O:57])[CH2:52][CH2:53][C:54]([OH:56])=[O:55]>C(#N)C>[C:51]([OH:58])(=[O:57])[CH2:52][CH2:53][C:54]([OH:56])=[O:55].[CH2:47]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH2:7][O:8][C:9](=[O:46])[CH2:10][CH2:11][NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([N:24]2[CH2:45][CH2:44][C:27]3([NH:31]/[C:30](=[N:32]/[C:33]([C:35]4[C:40]([NH2:41])=[N:39][C:38]([NH2:42])=[C:37]([Cl:43])[N:36]=4)=[O:34])/[NH:29][CH2:28]3)[CH2:26][CH2:25]2)=[O:23])[CH:17]=1)(=[O:15])=[O:14])=[O:6])[CH2:48][CH3:49]

Participants

5

Reactant 3

HCID 962WaterHCID 1110Succinic AcidHCID 178457291HCID 178457291, compound

Product 1

HCID 178457292HCID 178457292, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.5 g of 3-(3-{2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]decane-8-carbonyl}-benzenesulfonylamino)-propionic acid dipropylcarbamoylmethyl ester (may be prepared as in Preparation 1; 3.47 mmol) were dissolved in 25 mL acetonitrile and 1.5 mL water at 50° C. 409 mg succinic acid (3.47 mmol) was added. The acid dissolved immediately and the clear solution was cooled down to room temperature over 30 minutes. At approximately 30° C. the crystallization took place. The slurry was then stirred for approximately 16 h at room temperature. The crystals were collected by filtration. The filter cake was washed in portions with 9 ml acetonitrile/water 95:5 v/v and dried for 16 h at 50° C. and at around 10 mbar.

Workup

  1. customat 50° C
  2. dissolutionThe acid dissolved immediately
  3. customAt approximately 30° C. the crystallization
  4. filtrationThe crystals were collected by filtration
  5. washThe filter cake was washed in portions with 9 ml acetonitrile/water 95:5 v/v
  6. customdried for 16 h at 50° C. and at around 10 mbar

Sources & evidence

ORD record
ord-26c64cb81a9f407a802a9e5e9997f5bc
Source dataset
uspto-grants-2014_08
Patent number
US08809340B2

Reaction notes

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