Tetrahydrofuran → HCID 67355426, 화합물

HRID 627394

반응식

HRID 627394 반응식
C(OC([N:11]1[CH:16]2[CH2:17][N:18]([C:20]([C:22]3[CH:23]=[N:24][C:25]([NH:28][C:29]4[N:30]=[CH:31][C:32]5[CH:37]=[C:36]([C:38](=[O:42])[N:39]([CH3:41])[CH3:40])[N:35]([CH:43]6[CH2:47][CH2:46][CH2:45][CH2:44]6)[C:33]=5[N:34]=4)=[CH:26][CH:27]=3)=[O:21])[CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=O)C1C=CC=CC=1.C(CC(OC)=O)C.C1COCC1.[H][H]>[Pd].CO>[CH3:40][N:39]([CH3:41])[C:38]([C:36]1[N:35]([CH:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)[C:33]2[N:34]=[C:29]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([C:20]([N:18]4[CH2:17][CH:16]5[NH:11][CH:12]([CH2:13][O:14][CH2:15]5)[CH2:19]4)=[O:21])=[CH:23][N:24]=3)[N:30]=[CH:31][C:32]=2[CH:37]=1)=[O:42]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 12180Methyl butyrateHCID 67355740HCID 67355740, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67355426HCID 67355426, 화합물수율 93%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a round bottom flask was combined 7-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (0.461 g, 0.722 mmol), methanol ethyl acetate (12 ml), THF (3 ml), methanol (3 ml), and Pd on C/10%. The mixture was put under a balloon of hydrogen and stirred over night. The mixture was purged with nitrogen followed by addition of methylene chloride. The resultant mixture was filtered through a pad of celite. The celite was washed with additional methylene chloride. The organics were combined and concentrated to a residue. The residue was purified by silica gel chromotography which gave 7-Cyclopentyl-2-[5-(3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-7-carbonyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (338 mg, 0.67 mmol) in 93% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.82 (s, 1H), 8.63 (d, J=8.6 Hz, 1H), 8.56 (s, 1H), 8.47 (d, J=2.0 Hz, 1H), 7.87 (dd, J1=8.78 Hz, J2=2.26 Hz, 1H), 6.51 (s, 1H), 4.83 (m, 1H), 4.47 (s, 1H), 4.09 (m, 4H), 3.77 (s, 1H), 3.45-3.21 (m, 4H), 3.19 (s, 6H), 2.59 (m, 2H), 2.11 (m, 5H), 1.77 (m, 2H); HRMS m/z 505.2665 (M+H)+.

후처리

  1. customTo a round bottom flask was combined
  2. customThe mixture was purged with nitrogen
  3. additionfollowed by addition of methylene chloride
  4. filtrationThe resultant mixture was filtered through a pad of celite
  5. washThe celite was washed with additional methylene chloride
  6. concentrationconcentrated to a residue
  7. customThe residue was purified by silica gel chromotography which

출처 및 근거

ORD 기록
ord-68d491f440614a1d8e9700157cf69d2b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309252B2

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