1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90405361, compound

HRID 1505645Notes

Reaction equation

HRID 1505645 reaction equation
[S:1]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=1)(=[O:4])(=[O:3])[NH2:2].[N:16]1([C:22]2[C:23]3[CH:30]=[C:29]([CH2:31][C:32]([F:35])([F:34])[F:33])[S:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:15]=[C:13]([N:19]1[CH2:18][CH2:17][N:16]([C:22]2[C:23]3[CH:30]=[C:29]([CH2:31][C:32]([F:34])([F:33])[F:35])[S:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:21][CH2:20]1)[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][S:1]([NH2:2])(=[O:3])=[O:4])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 90404771HCID 90404771, compoundHCID 90405227HCID 90405227, compound

Product 1

HCID 90405361HCID 90405361, compoundYield 110.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

23 mg of 2-(4-(sulfamoylmethyl)phenyl)acetic acid (0.1 mmol), 20 mg of 4-(piperazin-1-yl)-6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidine (0.067 mmol), 20 mg of EDCI (0.1 mmol) and 4 mg of DMAP (0.033 mmol) was stirred in 2 mL of DCM. After 2 hs reaction mixture was concentrated and residue was loaded on silica gel column. Elution with DCM-MeOH 9:1 and evaporation of fraction produced 38 mg of (4-(2-oxo-2-(4-(6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl)ethyl)phenyl)methanesulfonamide (compound 44). 1H NMR (400 MHz, CDCl3): δ 8.44 (s, 1H), 7.36 (d, 2H, J=8 Hz), 7.25 (d, 2H, J=8 Hz), 7.20 (s, 1H), 4.88 (s, 2H), 4.26 (s, 1H), 3.5-4.0 (m, 10H). ESI MS [MH+]: 514.1. Its monohydrochloride salt was obtained by adding 1 equivalent of 1N HCl solution in diethyl ether to a solution of compound in ethanol.

Workup

  1. customAfter 2 hs reaction mixture
  2. concentrationwas concentrated
  3. washElution
  4. customwith DCM-MeOH 9:1 and evaporation of fraction

Sources & evidence

ORD record
ord-6d117cb626df45b5b2d3c2f9c6af36eb
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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