Ammonia → HCID 483407, compound

HRID 1625104Notes

Reaction equation

HRID 1625104 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)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 7914Diisopropyl EtherSolvent

Procedure

Crystalline form 1 of maraviroc phosphate (5 gm) was dissolved in diisopropyl 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 diisopropyl 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 diisopropyl 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-f9da978d16f042bdbe40308188d473a9
Source dataset
uspto-grants-2014_07
Patent number
US08779143B2

Reaction notes

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