Acetonitrile → 3-[2-{[3-(Diethylamino)-propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-n-propylbenzamide ethanedisulfonate salt hydrate

HRID 2243683Notes

Reaction equation

HRID 2243683 reaction equation
C(#N)C.[CH2:4]([N:6]([CH2:43][CH3:44])[CH2:7][CH2:8][CH2:9][NH:10][C:11]1[N:12]=[C:13]([C:30]2[CH:31]=[C:32]([CH:39]=[CH:40][C:41]=2[CH3:42])[C:33]([NH:35][CH2:36][CH2:37][CH3:38])=[O:34])[C:14]2[CH2:19][NH:18][C:17](=[O:20])[N:16]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[F:28])[C:15]=2[N:29]=1)[CH3:5].[CH2:45]([S:51]([OH:54])(=[O:53])=[O:52])[CH2:46][S:47]([OH:50])(=[O:49])=[O:48]>CO>[OH2:20].[CH2:45]([S:51]([OH:54])(=[O:53])=[O:52])[CH2:46][S:47]([OH:50])(=[O:49])=[O:48].[CH2:43]([N:6]([CH2:4][CH3:5])[CH2:7][CH2:8][CH2:9][NH:10][C:11]1[N:12]=[C:13]([C:30]2[CH:31]=[C:32]([CH:39]=[CH:40][C:41]=2[CH3:42])[C:33]([NH:35][CH2:36][CH2:37][CH3:38])=[O:34])[C:14]2[CH2:19][NH:18][C:17](=[O:20])[N:16]([C:21]3[C:22]([F:28])=[CH:23][CH:24]=[CH:25][C:26]=3[F:27])[C:15]=2[N:29]=1)[CH3:44]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 80321,2-Ethanedisulfonic AcidHCID 119499263-[2-{[3-(diethylamino)propyl]-amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide

Product 1

HCID 1317279773-[2-{[3-(Diethylamino)-propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-n-propylbenzamide ethanedisulfonate salt hydrateYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Acetonitrile (450 uL) was added to the crystalline 3-[2-{[3-(diethylamino)propyl]-amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide-free-base (25.0 mg), and the resulting mixture was heated to 50° C. Ethanedisulfonic acid was added (1.1 equivalents; 1M in methanol). The mixture was cooled to room temperature and stirred several hours. The product was filtered and dried for at least one hour in a vacuum oven at 50° C. with a slow nitrogen bleed. The yield was 62.0% (20.7 mg) of 3-[2-{[3-(diethylamino)-propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide ethanedisulfonate salt hydrate with a melting onset at <100° C. (determined by DSC).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe product was filtered
  3. customdried for at least one hour in a vacuum oven at 50° C. with a slow nitrogen

Sources & evidence

ORD record
ord-a6f9a0d012fe4755a929273bdf2a3e11
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

Loading…