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

HRID 1787058Notes

Reaction equation

HRID 1787058 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.Cl.C(OCC)(=O)C>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[ClH:1].[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

9

Reactant 5

HCID 681523-Hydroxypropionic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21866389Hydrogen chloride-ethyl acetateHCID 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 67520297N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-3-hydroxypropanamide hydrochloride

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 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 (300 mg), 3.6 M aqueous solution (0.25 mL) of 3-hydroxypropanoic acid, 1-hydroxybenzotriazole monohydrate (231 mg), N-[3-(dimethylamino)propyl]-N-ethylcarbodiimide hydrochloride (330 mg), triethylamine (0.8 mL) and N,N-dimethylformamide (3 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 (2 mL), and 4N hydrochloric acid-ethyl acetate (0.1 mL) was added. The obtained product was recrystallized from ethyl acetate to give the title compound (63.1 mg) as a white powder.

Workup

  1. customThe obtained product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3be30a51c2174b4691e184d20740a5a4
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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