Sodium Hydroxide → alisertib sodium anhydrous

HRID 241542Notes

Reaction equation

HRID 241542 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]2[C:6]3[N:23]=[C:22]([NH:24][C:25]4[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[C:27]([O:34][CH3:35])[CH:26]=4)[N:21]=[CH:20][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=3[F:19])[C:4]=2[CH:3]=1.[OH-].[Na+:39]>C(O)C>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]2[C:6]3[N:23]=[C:22]([NH:24][C:25]4[CH:33]=[CH:32][C:28]([C:29]([O-:31])=[O:30])=[C:27]([O:34][CH3:35])[CH:26]=4)[N:21]=[CH:20][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=3[F:19])[C:4]=2[CH:3]=1.[Na+:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24771867Alisertib

Product 1

HCID 66819785alisertib sodium anhydrous

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 mg of 4-{[9-chloro-7-(2-fluoro-6-methoxyphenyl) -5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino}-2-methoxybenzoic acid was stirred in 4 mL of ethanol in a screw-top vial. 1.1 mol equivalents of sodium hydroxide solution (406 μL, 1.044 M in water) were added. The solid dissolved followed by formation of a yellow precipitate. The sample was a mixture of Form 4 and Form 24. The solid was washed with 10 mL of ethanol and 20 mL of diethyl ether, and dried under vacuum at 70° C. for 2 days, and at 60° C. for a further 3 days to give Form 24. XRPD data for Form 24 is shown in FIG. 17 and Table 7; DSC data is shown in FIG. 18; TGA data is shown in FIG. 19.

Workup

  1. dissolutionThe solid dissolved
  2. additiona mixture of Form 4 and Form 24
  3. washThe solid was washed with 10 mL of ethanol and 20 mL of diethyl ether
  4. customdried under vacuum at 70° C. for 2 days
  5. customat 60° C. for a further 3 days to give Form 24

Sources & evidence

ORD record
ord-fe1c3d2099624660b0be18ab303f956d
Source dataset
uspto-grants-2014_02
Patent number
US08653064B2

Reaction notes

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