Ammonia → HCID 483407, compound

HRID 1625099Notes

Reaction equation

HRID 1625099 reaction equation
[CH3:1][C:2]1[N:6]([C@H:7]2[CH2:13][C@H:12]3[N:14]([CH2:15][CH2:16][C@H:17]([NH:24][C:25]([CH:27]4[CH2:32][CH2:31][C:30]([F:34])([F:33])[CH2:29][CH2:28]4)=[O:26])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C@H:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]([CH:35]([CH3:37])[CH3:36])=[N:4][N:3]=1.P([O-])([O-])([O-])=O.N.C1CCCCC1>O>[CH:35]([C:5]1[N:6]([CH:7]2[CH2:13][CH:12]3[N:14]([CH2:15][CH2:16][C@H:17]([NH:24][C:25]([CH:27]4[CH2:28][CH2:29][C:30]([F:34])([F:33])[CH2:31][CH2:32]4)=[O:26])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:2]([CH3:1])=[N:3][N:4]=1)([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8078CyclohexaneHCID 178434041HCID 178434041, compound

Product 1

HCID 483407HCID 483407, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Maraviroc phosphate (60 gm) was dissolved in water (400 ml) and pH of the reaction mass was adjusted to 8.0 to 8.5 with ammonia solution (30 ml). The layers were separated and the aqueous layer was extracted with methylene chloride. The organic layer was dried with sodium sulfate and treated with carbon. The methylene chloride was distilled off under vacuum at below 45° C. to obtain residual mass. To the residual mass was added cyclohexane (400 ml) and stirred for 15 minutes at room temperature, filtered. The solid obtained was dried under vacuum at 85° C. for 12 hours to obtain 47 gm of maraviroc amorphous form (HPLC Purity: 99.95%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. additiontreated with carbon
  5. distillationThe methylene chloride was distilled off under vacuum at below 45° C.
  6. customto obtain residual mass
  7. filtrationfiltered
  8. customThe solid obtained
  9. customwas dried under vacuum at 85° C. for 12 hours

Sources & evidence

ORD record
ord-9306f5d868bb4959abcc5443f4903e4e
Source dataset
uspto-grants-2014_07
Patent number
US08779143B2

Reaction notes

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