Ammonia → HCID 483407, compound

HRID 1625103Notes

Reaction equation

HRID 1625103 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(OC)(C)(C)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 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Crystalline form 1 of maraviroc phosphate (5 gm) was dissolved in methyl tert-butyl ether (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 methyl tert-butyl ether 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 20 minutes at room temperature, filtered. The solid obtained was dried to obtain 3.4 gm of maraviroc amorphous form.

Workup

  1. dry with materialThe separated organic layer was dried with sodium sulfate
  2. additiontreated with carbon
  3. distillationThe methyl tert-butyl ether was distilled off under vacuum at below 45° C.
  4. customto obtain residual mass
  5. stirringstirred for 20 minutes at room temperature
  6. filtrationfiltered
  7. customThe solid obtained
  8. customwas dried

Sources & evidence

ORD record
ord-0cb02447ea6c4c04b0dcc533ed9b33b6
Source dataset
uspto-grants-2014_07
Patent number
US08779143B2

Reaction notes

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