Fumaric Acid → HCID 86619557, compound

HRID 1869593Notes

Reaction equation

HRID 1869593 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[C:38]([NH2:45])=[C:37]([Cl:46])[CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:47]=[CH:48][CH:49]=[CH:50][C:4]=2[NH:3]1.[C:51]([OH:58])(=[O:57])/[CH:52]=[CH:53]/[C:54]([OH:56])=[O:55]>C(O)C>[C:51]([OH:58])(=[O:57])/[CH:52]=[CH:53]/[C:54]([OH:56])=[O:55].[C:51]([OH:58])(=[O:57])/[CH:52]=[CH:53]/[C:54]([OH:56])=[O:55].[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:43])([F:42])[F:44])[C:38]([NH2:45])=[C:37]([Cl:46])[CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:47]=[CH:48][CH:49]=[CH:50][C:4]=2[NH:3]1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 11629090HCID 11629090, compound

Product 1

HCID 86619557HCID 86619557, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
45 °C

Procedure

2.5 g (2.95 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate are dissolved in 25 ml of ethanol at ambient temperature, combined with 685 mg (5.9 mmol) fumaric acid and heated to 45° C. A viscous suspension is formed, which is diluted by the addition of 15 ml of ethanol. The mixture is heated to 70° C., during which time a white precipitate is formed. The suspension formed is diluted with another 5 ml of ethanol, cooled to 26° C. and filtered. The isolated solid is dried for 12 hours at 60° C.

Workup

  1. customA viscous suspension is formed
  2. temperatureThe mixture is heated to 70° C., during which time a white precipitate
  3. customis formed
  4. customThe suspension formed
  5. temperaturecooled to 26° C.
  6. filtrationfiltered
  7. customThe isolated solid is dried for 12 hours at 60° C.

Sources & evidence

ORD record
ord-dbd8f2746ad946bca9b61da5814ba9c7
Source dataset
uspto-grants-2009_12
Patent number
US07638625B2

Reaction notes

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