1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178425806, compound

HRID 541412Notes

Reaction equation

HRID 541412 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)=[O:19])[CH:15]=[CH:14][C:13]=1[CH3:34])=S.CCN=C=NCCCN(C)C>CN(C=O)C>[NH:1]1[C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]=[C:9]1[NH:11][C:12]1[CH:17]=[C:16]([CH:15]=[CH:14][C:13]=1[CH3:34])[C:18]([N:20]1[CH2:21][CH2:22][CH:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=2)[CH2:24][CH2:25]1)=[O:19]

Participants

4

Reactant 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86672543HCID 86672543, compound

Product 1

HCID 178425806HCID 178425806, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-aminopyridin-3-yl)-3-(5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-methylphenyl)thiourea (281.2) in DMF continued from the prior step was added EDCI (0.12 g, 0.64 mmol). The mixture was stiffed at room temperature overnight. The DMF was removed under high vacuum and the residue was purified using prep.-TLC (5% MeOH in EtOAc) to yield 76 mg (56% for 3 steps) of a white powder. m/z (ES+) 437 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (br, 1H), 8.48 (s, 1H), 8.40 (s, 1H), 8.08 (d, 1H), 7.78 (d, 2H), 7.53 (d, 2H), 7.29 (d, 2H), 7.05 (d, 1H), 4.65 (m, 1H), 3.91 (m, 1H), 3.17 (m, 1H), 3.04-3.72 (m, 2H), 2.36 (s, 3H), 1.97-1.60 (m, 4H).

Workup

  1. customThe DMF was removed under high vacuum
  2. customthe residue was purified
  3. customto yield 76 mg (56% for 3 steps) of a white powder

Sources & evidence

ORD record
ord-450fea27bbe4488aa142f76152a6fed4
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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