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Thionyl Chloride → HCID 178425047, 화합물

HRID 1898398
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HRID 1898398 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([OH:26])=O)=[CH:15][C:13]=2[N:14]=1.S(Cl)(Cl)=O.[F:31][C:32]([F:44])([F:43])[C:33]1[CH:34]=[C:35]([C:39]2([NH2:42])[CH2:41][CH2:40]2)[CH:36]=[CH:37][CH:38]=1.CCN(C(C)C)C(C)C>C1COCC1.C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([NH:42][C:39]3([C:35]4[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([F:31])([F:43])[F:44])[CH:34]=4)[CH2:41][CH2:40]3)=[O:26])=[CH:15][C:13]=2[N:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 431465831-(3-(Trifluoromethyl)phenyl)cyclopropanamineHCID 178425067HCID 178425067, 화합물

생성물 1

HCID 178425047HCID 178425047, 화합물수율 5.4%

시약·촉매·용매 2

HCID 241
Benzene
용매
HCID 8028Tetrahydrofuran용매

실험 절차

The title compound was prepared following the procedure described for Example-108 using 2-[(2-chloro-6-methylphenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-35, 0.150 g, 0.403 mmol), thionyl chloride (2.0 mL), 1-(3-(trifluoromethyl)phenyl)cyclopropanamine (Intermediate-44, 0.121 g, 0.604 mmol), benzene (4 mL), THF (6.0 mL) and DIPEA (4 mL). The obtained crude product was purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH:DCM to afford 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.33-1.56 (m, 4H), 1.51 (s, 6H), 2.23 (s. 1H), 3.07 (s, 2H), 7.29-7.42 (m, 4H), 7.49-7.53 (m, 3H), 8.40 (s, 1H), 8.93 (s, 1H), 10.86 (s, 1H); MS [M+H]+: 555.29.

후처리

  1. customThe title compound was prepared
  2. customThe obtained crude product
  3. customwas purified by column chromatography on basic alumina eluting with 0.7-1.0% MeOH

출처 및 근거

ORD 기록
ord-cdb7e3fcefcc44b887ef7a33c5ee6b06
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08519149B2

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