Fumaric Acid → HCID 50913437, compound

HRID 471086Notes

Reaction equation

HRID 471086 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:46][CH2:45][C:29]3([O:34][CH2:33][CH2:32][N:31]([C:35]([C:37]4[N:38]=[C:39]([CH:42]([CH3:44])[CH3:43])[S:40][CH:41]=4)=[O:36])[CH2:30]3)[CH2:28][CH2:27]2)=[CH:21][C:3]=1[CH2:4][CH2:5][NH:6][CH2:7][C@@H:8]([C:10]1[C:18]2[S:17][C:16](=[O:19])[NH:15][C:14]=2[C:13]([OH:20])=[CH:12][CH:11]=1)[OH:9].[C:47]([OH:54])(=[O:53])/[CH:48]=[CH:49]/[C:50]([OH:52])=[O:51]>C(O)C>[C:47]([OH:54])(=[O:53])/[CH:48]=[CH:49]/[C:50]([OH:52])=[O:51].[F:1][C:2]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:27][CH2:28][C:29]3([O:34][CH2:33][CH2:32][N:31]([C:35]([C:37]4[N:38]=[C:39]([CH:42]([CH3:44])[CH3:43])[S:40][CH:41]=4)=[O:36])[CH2:30]3)[CH2:45][CH2:46]2)=[CH:21][C:3]=1[CH2:4][CH2:5][NH:6][CH2:7][C@@H:8]([C:10]1[C:18]2[S:17][C:16](=[O:19])[NH:15][C:14]=2[C:13]([OH:20])=[CH:12][CH:11]=1)[OH:9]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 49855236HCID 49855236, compound

Product 1

HCID 50913437HCID 50913437, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

(R)-7-(2-(2-fluoro-5-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one (2.4 g) was dissolved in ethanol (240 mL) at 50° C. Fumaric acid (0.416 g) was added and the mixture heated under reflux until a clear solution formed. The resulting solution was allowed to cool to 60° C. and seeded with form A (example 47C) (50 mg). The resulting mixture was stirred overnight at 50° C. and then allowed to cool to RT over 3 hrs. The resulting white solid was isolated by filtration, washed with ethanol (50 mL), ether (2×200 mL) and sucked dry to give the titled compound as a white solid. Yield 2.3 g.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux until a clear solution
  3. customformed
  4. temperatureto cool to RT over 3 hrs
  5. customThe resulting white solid was isolated by filtration
  6. washwashed with ethanol (50 mL), ether (2×200 mL)
  7. customsucked dry

Sources & evidence

ORD record
ord-b816b2ee8020415e8a8b9053c1ed0522
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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