Salicylic Acid → HCID 25256628, compound

HRID 1038361Notes

Reaction equation

HRID 1038361 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][C@@H:13]([O:34][C:35]([N:37]2[CH2:42][CH2:41][CH:40]([N:43]3[CH2:49][CH2:48][C:47]4[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=4[NH:45][C:44]3=[O:54])[CH2:39][CH2:38]2)=[O:36])[C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])=[CH:4][C:3]=1[Cl:55].[C:56]([OH:65])(=[O:64])[C:57]1[C:58](=[CH:60][CH:61]=[CH:62][CH:63]=1)[OH:59]>C(O)C>[C:56]([OH:65])(=[O:64])[C:57]1[C:58](=[CH:60][CH:61]=[CH:62][CH:63]=1)[OH:59].[NH2:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][C:5]([CH2:12][C@@H:13]([O:34][C:35]([N:37]2[CH2:38][CH2:39][CH:40]([N:43]3[CH2:49][CH2:48][C:47]4[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=4[NH:45][C:44]3=[O:54])[CH2:41][CH2:42]2)=[O:36])[C:14]([N:16]2[CH2:17][CH2:18][N:19]([CH:22]3[CH2:23][CH2:24][N:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:26][CH2:27]3)[CH2:20][CH2:21]2)=[O:15])=[CH:4][C:3]=1[Cl:55]

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 25164163HCID 25164163, compound

Product 1

HCID 25256628HCID 25256628, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

250 mg ethyl 4-[4-[(2R)-3-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-1-oxo-2-[[[4-(1,2,4,5-tetrahydro-2-oxo-3H-1,3-benzodiazepin-3-yl)-1-piperidinyl]carbonyl]oxy]propyl]-1-piperazinyl]-piperidine-1-acetate (0.316 mmol) are dissolved in 1.5 ml of ethanol at ambient temperature. The solution is heated to 80° C. and combined with a solution of 43 mg salicylic acid (0.361 mmol) in 1.5 ml of ethanol. The temperature is lowered by 5° C. every 30 minutes. Then the solution is stirred for 12 hours at ambient temperature. As no precipitate has formed, the solvent is distilled off and the residue is dissolved in 2.5 ml methylisobutylketone at 80° C. The temperature is lowered by 5° C. every 30 minutes. Then the solution is stirred for 12 hours at ambient temperature. Then the solution is stirred for a further 24 hours in the open vessel during which time the solvent evaporates. The resultant solid is filtered off, washed with methylisobutylketone and dried for 12 hours at 35° C.

Workup

  1. customAs no precipitate has formed
  2. distillationthe solvent is distilled off
  3. dissolutionthe residue is dissolved in 2.5 ml methylisobutylketone at 80° C
  4. waitThe temperature is lowered by 5° C. every 30 minutes
  5. stirringThen the solution is stirred for 12 hours at ambient temperature
  6. stirringThen the solution is stirred for a further 24 hours in the open vessel during which time the solvent
  7. customevaporates
  8. filtrationThe resultant solid is filtered off
  9. washwashed with methylisobutylketone
  10. customdried for 12 hours at 35° C.

Sources & evidence

ORD record
ord-9caacdfcfde843009492cb39f8d279ec
Source dataset
uspto-grants-2013_10
Patent number
US08551987B2

Reaction notes

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