Hydrochloric Acid → Milveterol

HRID 502004Notes

Reaction equation

HRID 502004 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:13].Cl.[OH:15][C@H:16]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:17][NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:28][C@H:29]([OH:40])[C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:37][CH:38]=[O:39])[CH:31]=2)=[CH:21][CH:20]=1.[OH-].[Na+].Cl>O>[ClH:13].[OH:15][C@H:16]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:17][NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:28][C@H:29]([OH:40])[C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:37][CH:38]=[O:39])[CH:31]=2)=[CH:21][CH:20]=1.[OH:15][C@H:16]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:17][NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:28][C@H:29]([OH:40])[C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:37][CH:38]=[O:39])[CH:31]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 9892481Milveterol

Product 2

HCID 9892481MilveterolHCID 11225217Milveterol hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a scintillation vial, water (10 mL) was added to the dihydrochloride salt of compound 1 (402 mg, 0.79 mmol) to form a slurry. The pH was adjusted with 1.0 N NaOH and 1.0 N HCl to 5.09 and the slurry was stirred for 48 h. The pH of the slurry was measured at 5.57. The slurry was vacuum filtered using a Buchner funnel and the filter paper was removed and allowed to air dry for 3 days to yield the monohydrochloride salt of compound 1.

Workup

  1. customto form a slurry
  2. filtrationfiltered
  3. customthe filter paper was removed
  4. customto air dry for 3 days

Sources & evidence

ORD record
ord-5420b41f6b0643988f2428eed0c1e8f0
Source dataset
uspto-grants-2010_08
Patent number
US07772434B2

Reaction notes

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