1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18516856, compound

HRID 1370092Notes

Reaction equation

HRID 1370092 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[C:12]([C:20]#[N:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=2)[CH2:25][CH2:24]1.[Li].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.CN1CCOCC1>[C:20]([C:12]1[C:13]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[N:14][C:9]([NH:8][C:4]2[CH:3]=[C:2]([NH:1][C:34](=[O:35])[C:33]3[CH:32]=[CH:31][C:30]([CH2:29][N:26]4[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]4)=[CH:38][CH:37]=3)[CH:7]=[CH:6][CH:5]=2)=[N:10][CH:11]=1)#[N:21]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3028194LithiumHCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acidHCID 18516946HCID 18516946, compound

Product 1

HCID 18516856HCID 18516856, compound

Reagents, catalysts & solvents 2

HCID 79724-MethylmorpholineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of N-3-aminophenyl-5-cyano-4-thien-2-ylpyrimidine-2-amine (300 mg, 1.0 mmol) and 4-(4-methylpiperazin-1-yl)methylbenzoic acid, lithium salt (300 mg, 1.0 mmol) in DMF (10 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (307 mg, 1.6 mmol), 1-hydroxybenzotriazole (216 mg, 1.6 mmol) and N-methylmorpholine (350 ml, 3.2 μmol) and the resulting mixture was stirred at ambient temperature for 48 h. The reaction was then concentrated under reduced pressure and the resulting residue partitioned between ethyl acetate and saturated brine. The organic phase was dried (MgSO4), concentrated under reduced pressure and the resulting residue recrystallised from ethyl acetate-ether-MeOH (4:4:1) to give the title compound (312 mg) as a colourless solid, m.p. 208-209°. δH (d6 DMSO) 10.48 (1H, bs), 10.23 (1H, s), 8.89 (1h,s), 8.28 (1H, d, J 3.5 Hz), 8.13 (1H, m), 7.98 (1H, d, J 4.8 Hz), 7.90 (2H, d, J 8.2 Hz), 7.60 (1H, bs), 7.43 (3H, d, J 8.2 Hz), 7.36-7.30 (2H, s), 3.52 (2H, s), 2.37 (8H, bs) and 2.15 (3H,s).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customthe resulting residue partitioned between ethyl acetate and saturated brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue recrystallised from ethyl acetate-ether-MeOH (4:4:1)

Sources & evidence

ORD record
ord-956d35c3f1684915a02391644ea8d9c3
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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