Methanesulfonic Acid → N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide methanesulfonate

HRID 1787064Notes

Reaction equation

HRID 1787064 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][NH:31][C:32](=[O:36])[CH2:33][CH2:34][OH:35])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.Cl.Cl.NCCN1C2C(NC3C=CC(OC4C=CC=C(C(F)(F)F)C=4)=C(Cl)C=3)=NC=NC=2C=C1.OCCC(O)=O.O.ON1C2C=CC=CC=2N=N1.[CH3:87][S:88]([OH:91])(=[O:90])=[O:89]>C(OCC)(=O)C.CN(C)C=O.O1CCCC1.C(N(CC)CC)C>[CH3:87][S:88]([OH:91])(=[O:90])=[O:89].[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][NH:31][C:32](=[O:36])[CH2:33][CH2:34][OH:35])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1

Participants

10

Reactant 5

HCID 6395Methanesulfonic AcidHCID 681523-Hydroxypropionic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 56849850N-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide2×HCID 568513565-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride

Product 1

HCID 56849849N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide methanesulfonate

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide was obtained by the reaction in the same manner as in Example 202 (iii) using 5-(2-aminoethyl)-N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (3.50 g), a 3.6 M aqueous solution (5.6 mL) of 3-hydroxypropanoic acid, 1-hydroxybenzotriazole monohydrate (4.56 g), N-[3-(dimethylamino)propyl]-N-ethylcarbodiimide hydrochloride (10.1 g), triethylamine (10 mL) and a mixed solvent of tetrahydrofuran (17 mL)/N,N-dimethylformamide (17 mL). The obtained N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide was dissolved in ethyl acetate (50 mL), methanesulfonic acid (0.155 mL) was added, and the mixture was stirred for 2 hrs. The reaction mixture was concentrated under reduced pressure and recrystallized from ethyl acetate to give the title compound (1.04 g) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3089ba9acaa543c69e2a13e4bc2e376d
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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