1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44603208, 화합물

HRID 79072노트

반응식

HRID 79072 반응식
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]2[CH:16]=[N:17][S:18][C:14]=2[CH:13]=[CH:12][C:11]=1[C:19]([OH:21])=O.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:41][O:42][CH2:43][C@@H:44]([OH:46])[CH3:45].CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[OH:46][C@@H:44]([CH3:45])[CH2:43][O:42][NH:41][C:19]([C:11]1[CH:12]=[CH:13][C:14]2[S:18][N:17]=[CH:16][C:15]=2[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])=[O:21]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11788308(2S)-1-(aminooxy)propan-2-olHCID 670836404-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid

생성물 1

HCID 44603208HCID 44603208, 화합물수율 26%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(2-fluoro-4-iodo-phenylamino)-benzo[d]iso-thiazole-5-carboxylic acid (150 mg, 0.362 mmol), diisopropylethylamine (0.25 mL, 1.45 mmol), HOBt (98 mg, 0.724 mmol) and (S)-1-aminooxy-propan-2-ol (92 mg, 0.724 mmol in DMF (2 mL) was added EDCI (139 mg, 0.724 mmol). The reaction mixture was stirred for 16 hours at room temperature, diluted with ethyl acetate, and washed with water, a saturated aqueous solution of sodium hydrogen carbonate, then brine before being dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 30% to 80%, EtOAc in cyclohexane) to afford the title compound as a solid (45 mg, 26%). LCMS (method A): RT=10.26 min, [M+H]+=488. 1H NMR (DMSO-d6, 400 MHz) 11.72 (1 H, s), 9.22 (1 H, s), 8.69 (1 H, s), 7.86-7.81 (1 H, m), 7.64-7.55 (2 H, m), 7.30 (1 H, dd, J=8.47, 1.83 Hz), 6.63 (1 H, t, J=8.72 Hz), 4.73 (1 H, s), 3.76-3.68 (1 H, m), 3.53 (2 H, d, J=5.78 Hz), 0.99 (3 H, d, J=6.33 Hz).

후처리

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, then brine before being dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8726a66eaf8c4a79bd305952e17a829b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841462B2

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