1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67520930, compound

HRID 1926081Notes

Reaction equation

HRID 1926081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:20][C:21]2[C:22]3[N:29]([CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:28]=[CH:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1.Cl.Cl.NCCCN1C2C(NC3C=CC(OC4C=CC=C(OC(F)(F)F)C=4)=C(Cl)C=3)=NC=NC=2C=C1.CS(CC(O)=O)(=O)=O.Cl.C(N=C=NCCCN(C)C)C.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:20][C:21]2[C:22]3[N:29]([CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:28]=[CH:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:18])([F:19])[F:17])[CH:10]=1

Participants

10

Reactant 6

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 37328412-Methanesulfonylacetic acidHCID 21866389Hydrogen chloride-ethyl acetateHCID 57597273HCID 57597273, compound2×HCID 86626252HCID 86626252, compound

Product 1

HCID 67520930HCID 67520930, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{3-[4-({3-Chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propyl}-2-(methylsulfonyl)acetamide was obtained by the reaction in the same manner as in Example 155 (iv) using 5-(3-aminopropyl)-N-{3-chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride (170 mg), 2-(methylsulfonyl)acetic acid (85.0 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (177 mg), 1-hydroxybenzotriazole monohydrate (141 mg), triethylamine (0.43 mL) and N,N-dimethylformamide (5.0 mL). To a solution of N-{3-[4-({3-chloro-4-[3-(trifluoromethoxy)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propyl}-2-(methylsulfonyl)acetamide in ethyl acetate (1.0 mL) was added 4N hydrochloric acid-ethyl acetate (0.50 mL) at room temperature, and the mixture was stirred at room temperature for 1 hr. After concentration under reduced pressure, diisopropyl ether was added, and the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether to give the title compound (128 mg) as colorless powder crystals.

Workup

  1. concentrationAfter concentration under reduced pressure, diisopropyl ether
  2. additionwas added
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-0e3a91d779d849e49e54ea50f68403a3
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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