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

HRID 1370092노트

반응식

HRID 1370092 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 18516856HCID 18516856, 화합물

시약·촉매·용매 2

HCID 79724-Methylmorpholine촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-956d35c3f1684915a02391644ea8d9c3
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06579983B1

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