1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178520720, compound

HRID 1257689Notes

Reaction equation

HRID 1257689 reaction equation
[N:1]1([C@H:13]2[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14]2)[C:12]2[C:4](=[CH:5][N:6]=[C:7]3[C:11]=2[CH:10]=[CH:9][NH:8]3)[N:3]=[N:2]1.[F:19][C:20]([F:26])([F:25])[CH2:21][C:22](O)=[O:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[F:19][C:20]([F:26])([F:25])[CH2:21][C:22]([NH:18][C@H:15]1[CH2:16][CH2:17][C@H:13]([N:1]2[C:12]3[C:4](=[CH:5][N:6]=[C:7]4[C:11]=3[CH:10]=[CH:9][NH:8]4)[N:3]=[N:2]2)[CH2:14]1)=[O:23]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27779723,3,3-Trifluoropropionic acidHCID 178511584HCID 178511584, compound

Product 1

HCID 178520720HCID 178520720, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of racemic trans 3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamine (120 mg, 0.49 mmol) in DMF (3 mL), 3,3,3-trifluoropropionic acid (53.0 μL, 0.60 mmol), DMAP (103 mg, 0.84 mmol), HOBt (100 mg, 0.74 mmol) and EDCI (161 mg, 0.84 mmol) were added. Stirring was continued for 18 hours at ambient temperature. The mixture was diluted with water and purified by column chromatography (SCX-2, gradient: methanol to 2M NH3 in methanol). The isolated product was triturated (DCM), washed with water and dried in vacuo at 40° C. for 18 hours affording 79.8 mg (45%) of racemic trans 3,3,3-trifluoro-N-[3-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-propionamide as a grey powder. LCMS (Method A, ESI): RT=3.14 min, m+H=353.3; 1H NMR (400 MHz, DMSO) δ: 12.37 (s, 1H), 9.00 (s, 1H), 8.53 (d, 1H), 7.61 (t, 1H), 7.00 (dd, 1H), 5.67 (m, 1H), 4.48 (m, 1H), 3.26 (q, 2H), 2.55 (m, 2H), 2.33-2.18 (m, 3H), 1.71 (m, 1H).

Workup

  1. custompurified by column chromatography (SCX-2, gradient: methanol to 2M NH3 in methanol)
  2. customThe isolated product was triturated (DCM)
  3. washwashed with water
  4. customdried in vacuo at 40° C. for 18 hours

Sources & evidence

ORD record
ord-56ffa1bcb49d45a68ed0d35a4899e01a
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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