1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67520514, compound

HRID 1787054Notes

Reaction equation

HRID 1787054 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][C:31]([NH:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])=[O:32])[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.ClC1C=C(NC2C3N(CCC(O)=O)C=CC=3N=CN=2)C=CC=1OC1C=CC=C(C(F)(F)F)C=1.CS(CCN)(=O)=O.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.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][C:31]([NH:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])=[O:32])[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:16])[F:17])[CH:10]=1

Participants

10

Reactant 6

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 43405612-(Methylsulfonyl)ethanamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 57597246HCID 57597246, compound2×HCID 67520195HCID 67520195, compound

Product 1

HCID 67520514HCID 67520514, compoundYield 160%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]-N-[2-(methylsulfonyl)ethyl]propanamide (140 mg) was obtained by the reaction in the same manner as in Example 202 (iii) using 3-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propanoic acid (199 mg), 2-(methylsulfonyl)ethanamine (106 mg), 1-hydroxybenzotriazole monohydrate (84.7 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (128.6 mg), triethylamine (0.1 mL) and N,N-dimethylformamide (2 mL). The obtained 3-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]-N-[2-(methylsulfonyl)ethyl]propanamide was dissolved in ethyl acetate (2 mL), 4N hydrochloric acid-ethyl acetate (0.1 mL) was added, and the precipitate was collected by filtration and dried to give the title compound (119 mg) as a white powder.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-ae28bb6c867541d29f3282c7a18ac86e
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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