Ammonia → HCID 483407, compound

HRID 1625102Notes

Reaction equation

HRID 1625102 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>C(OCC)(=O)C.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 8078CyclohexaneHCID 178434041HCID 178434041, compound

Product 1

HCID 483407HCID 483407, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crystalline form 1 of maraviroc phosphate (5 gm) was dissolved in ethyl acetate (60 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 stirred for 15 minutes. The separated 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 (50 ml) and stirred for 15 minutes at room temperature, filtered. The solid obtained was dried to obtain 3.5 gm of maraviroc amorphous form.

Workup

  1. dry with materialThe separated organic layer was dried with sodium sulfate
  2. additiontreated with carbon
  3. distillationThe ethyl acetate was distilled off under vacuum at below 45° C.
  4. customto obtain residual mass
  5. stirringstirred for 15 minutes at room temperature
  6. filtrationfiltered
  7. customThe solid obtained
  8. customwas dried

Sources & evidence

ORD record
ord-854e958f687f450a9f307d676c926612
Source dataset
uspto-grants-2014_07
Patent number
US08779143B2

Reaction notes

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