HCID 87222433, 화합물 → HCID 87222515, 화합물

HRID 712276노트

반응식

HRID 712276 반응식
C(O[K])(C)(C)C.[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:28]=[N:29][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([O:41]CC)=[O:40])[CH2:35][CH2:34]4)=[N:31][CH:32]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]>CS(C)=O>[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:32]=[N:31][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([OH:41])=[O:40])[CH2:35][CH2:34]4)=[N:29][CH:28]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]

참가 물질

4

반응물 2

HCID 87222433HCID 87222433, 화합물HCID 178418922HCID 178418922, 화합물

생성물 1

HCID 87222515HCID 87222515, 화합물수율 40%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

tBuOK (124 mg, 1.11 mmol) was added to a solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate in DMSO (4 mL). The mixture was stirred at ambient temperature for 2 h after which time LCMS indicated clean conversion to the acid. The mixture was filtered through cotton wool to remove solid particulates and purified by preparative HPLC to give Compound 88 as a white solid, 76 mg, 40% yield over 2 steps. 1H NMR (DMSO-d6): δ 10.89 (1H, s), 8.85 (2H, s), 7.95 (1H, d, J=1.62 Hz), 7.76 (1H, d, J=1.69 Hz), 7.16 (1H, t, J=5.50 Hz), 4.32 (2H, dt, J=13.67, 4.40 Hz), 4.09 (3H, s), 3.38 (2H, ddd, J=13.49, 10.48, 3.40 Hz), 3.23 (2H, p, J=6.71 Hz), 2.42 (3H, s), 2.05 (2H, dt, J=13.34, 3.66 Hz), 1.41 (2H, ddd, J=13.34, 10.04, 3.92 Hz), 1.21 (3H, s), 1.14 (3H, t, J=7.15 Hz). MS: 512 [M+H]+.

후처리

  1. filtrationThe mixture was filtered through cotton wool
  2. customto remove solid particulates
  3. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-c049c60c51ae4d60aa26597ff75e326c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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