Sodium Chloride → HCID 66970399, compound

HRID 1363130Notes

Reaction equation

HRID 1363130 reaction equation
[CH3:1][O:2][C:3]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20]([NH:22][C@H:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=3)[O:26][CH2:25][CH2:24]2)[C:19]([N+:34]([O-])=O)=[CH:18][N:17]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1COCC1.O.CO>[CH3:1][O:2][C:3]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20]([NH:22][C@H:23]2[C:32]3[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=3)[O:26][CH2:25][CH2:24]2)[C:19]([NH2:34])=[CH:18][N:17]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 66970463HCID 66970463, compound

Product 1

HCID 66970399HCID 66970399, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-4-(2,4-dimethoxybenzylamino)-3-(4-(6-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)benzonitrile (prepared as described below in example 26, paragraph [0157]) (12 mg) in THF (5 mL) was added a premixed solution of sodium hydrosulfite (100 mg) and sodium bicarbonate (50 mg) in water (10 mL). MeOH (1 mL) was also added to aid solution of the mixture, which was stirred at room temperature for 30 min, when sodium chloride was added to saturate the solution. The resultant mixture was extracted with EtOAc (2×), the combined organics were dried, filtered and evaporated to yield (R)-4-(2,4-dimethoxybenzylamino)-3-(5-amino-4-(6-fluorochroman-4-ylamino)pyrimidin-2-ylamino)benzonitrile that was used as such for the next step, MH+=542.

Workup

  1. concentrationto saturate the solution
  2. extractionThe resultant mixture was extracted with EtOAc (2×)
  3. customthe combined organics were dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a2946be1145c409caaff8db9603f19a6
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…