Ammonia → HCID 483407, compound

HRID 1625105Notes

Reaction equation

HRID 1625105 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 1,113.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Crystalline form 1 of maraviroc phosphate (5 gm) was dissolved in water (40 ml) and pH of the reaction mass was adjusted to 8.0 to 8.5 with ammonia solution (4 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layer was dried with sodium sulfate and treated with carbon. The ethyl acetate 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.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. additiontreated with carbon
  5. distillationThe ethyl acetate 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-745cd1742d0747f3ad685bd06565386c
Source dataset
uspto-grants-2014_07
Patent number
US08779143B2

Reaction notes

Loading…