2-Propanol, reaction products with ammonia, distn. residues → Vemurafenib

HRID 1747256Notes

Reaction equation

HRID 1747256 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][N:14](C(=O)C4C(Cl)=CC=CC=4Cl)[C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1.N.C(O)(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:28])=[O:29])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 51001026N-(3-(5-(4-chlorophenyl)-1-(2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide

Product 1

HCID 42611257Vemurafenib

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a high pressure vessel is added compound 9 (1.70 kg, 2.567 mol) in THF (5 L), followed by an ammonia/isopropyl alcohol solution (30.80 mol of ammonia in 12 L of isopropyl alcohol). The mixture is heated to 100° C. overnight. When the reaction is completed, the solvents are removed in vacuum and the residue is dissolved in isopropanol. Compound 10 is isolated and further purified by recrystallization using a mixture of THF (7 L) and isopropanol (14 L). Yield: 0.763 kg (60.7%).

Workup

  1. customthe solvents are removed in vacuum
  2. dissolutionthe residue is dissolved in isopropanol

Sources & evidence

ORD record
ord-66a8408b121e45de96f4c940aaec7e07
Source dataset
uspto-grants-2015_10
Patent number
US09150570B2

Reaction notes

Loading…