Chloroform → ((3S)-1-((3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)pyrrolidin-3-yl)methanol

HRID 472102노트

반응식

HRID 472102 반응식
[NH:1]1[CH2:5][CH2:4][C@H:3]([CH2:6][OH:7])[CH2:2]1.C(Cl)(Cl)Cl.CCN(C(C)C)C(C)C.[CH3:21][CH:22]1[CH:27]([N:28]([CH3:48])[C:29]2[C:30]3[CH:37]=[CH:36][N:35]([S:38]([C:41]4[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=4)(=[O:40])=[O:39])[C:31]=3[N:32]=[CH:33][N:34]=2)[CH2:26][CH2:25][CH:24]([CH2:49][S:50](Cl)(=[O:52])=[O:51])[CH2:23]1>CN(C=O)C>[CH3:21][CH:22]1[CH:27]([N:28]([CH3:48])[C:29]2[C:30]3[CH:37]=[CH:36][N:35]([S:38]([C:41]4[CH:42]=[CH:43][C:44]([CH3:45])=[CH:46][CH:47]=4)(=[O:39])=[O:40])[C:31]=3[N:32]=[CH:33][N:34]=2)[CH2:26][CH2:25][CH:24]([CH2:49][S:50]([N:1]2[CH2:5][CH2:4][C@H:3]([CH2:6][OH:7])[CH2:2]2)(=[O:52])=[O:51])[CH2:23]1

참가 물질

6

반응물 4

HCID 6212Chloroform2회HCID 81531DiisopropylethylamineHCID 7446911(3S)-3-PyrrolidinemethanolHCID 86653967HCID 86653967, 화합물

생성물 1

HCID 67074420((3S)-1-((3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)pyrrolidin-3-yl)methanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of (S)-pyrrolidin-3-ylmethanol (0.150 g, 1.5 mmol), CHCl3 (5 mL) and DIEA (0.5 mL, 3 mmol) was treated with a mixture of (3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methanesulfonyl chloride (0.208 g, 0.41 mmol), CHCl3 (3.0 mL), and DMF (1.5 mL). After 1 h, the mixture was concentrated and the resulting residue was chromatographed using 0→8% MeOH in CH2Cl2. The product fractions were pooled and concentrated to give ((3S)-1-((3-methyl-4-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methylsulfonyl)pyrrolidin-3-yl)methanol (0.126 g (54%). MS for C27H37N5O5S2 (ESI) (MH)+ m/z=576.

후처리

  1. concentrationthe mixture was concentrated
  2. customthe resulting residue was chromatographed
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8ff31619476c4b458c4443b3a4463599
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633206B2

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