Dichloromethane → HCID 23729488, compound

HRID 1675687Notes

Reaction equation

HRID 1675687 reaction equation
Cl.[CH2:2]([N:4]1[C:8]2=[N:9][C:10]([CH2:45][CH3:46])=[C:11]([CH2:20][NH:21][C:22](=[O:44])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:43])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]([CH2:40][CH2:41][OH:42])[CH3:39])=[CH:25][CH:24]=3)[C:12]([NH:13][CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[C:7]2[CH:6]=[N:5]1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].ClCCl>C(OCC)(=O)C>[CH2:2]([N:4]1[C:8]2=[N:9][C:10]([CH2:45][CH3:46])=[C:11]([CH2:20][NH:21][C:22](=[O:44])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:43])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]([CH2:40][CH2:41][OH:42])[CH3:39])=[CH:25][CH:24]=3)[C:12]([NH:13][CH:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[C:7]2[CH:6]=[N:5]1)[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 23729487HCID 23729487, compound

Product 1

HCID 23729488HCID 23729488, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-4-({8-[(2-hydroxyethyl)(methyl)amino]octanoyl}amino)benzamide monohydrochloride (20.0 g, 0.0304 mol, e.g. optionally the Form 1 anhydrate thereof) was suspended in ethyl acetate (150 ml). Potassium carbonate (7.5 g in 50 ml water) was added dropwise, and the mixture was stirred vigorously for 3 hours. The solid was filtered off, washed with ethyl acetate (30 ml), and dried at 50° C. Analysis indicates that this product contains about 1.5% of chloride. The product was suspended in isopropanol (160 ml), and Dowex 550A resin (10 g) was added. The suspension was heated to 60° C. for 1 hour, and was filtered while hot. The filtrate was concentrated to leave a white foam. Dichloromethane (100 ml) was added and the resulting mixture was concentrated to dryness to give the title compound (the “free base”). Analysis indicates about 0.3% of chloride remaining; NMR analysis indicates about 0.3% of water present.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with ethyl acetate (30 ml)
  3. customdried at 50° C
  4. additionDowex 550A resin (10 g) was added
  5. filtrationwas filtered while hot
  6. concentrationThe filtrate was concentrated
  7. customto leave a white foam
  8. concentrationthe resulting mixture was concentrated to dryness

Sources & evidence

ORD record
ord-708f456b283a46d086587e31f14f092d
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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