Ammonia → HCID 483407, compound

HRID 1625101Notes

Reaction equation

HRID 1625101 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.CCCCCCC>C(Cl)Cl.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

6

Reactant 3

HCID 222AmmoniaHCID 8900HeptaneHCID 178434041HCID 178434041, compound

Product 1

HCID 483407HCID 483407, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Maraviroc phosphate (6 gm) was dissolved in methylene chloride (50 ml) and water (40 ml). The pH of the reaction mass was adjusted to 8.0 to 8.5 with ammonia solution (3 ml) and then the layers were separated. 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 n-heptane (40 ml) and stirred for 30 minutes at room temperature. The solid obtained was collected by filtration and dried to obtain 4.6 gm of maraviroc amorphous form (HPLC Purity: 99.96%).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. additiontreated with carbon
  4. distillationThe methylene chloride was distilled off under vacuum at below 45° C.
  5. customto obtain residual mass
  6. customThe solid obtained
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-6eefbe56ae1b49d6a79122b644b73a7d
Source dataset
uspto-grants-2014_07
Patent number
US08779143B2

Reaction notes

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