Iodine → tert-butyl 6-(5-(3-amino-6-(2-(2-cyanopropan-2-yl)pyridin-4-yl)pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 331510노트

반응식

HRID 331510 반응식
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.C(N(CC)CC)C.[NH2:29][C:30]1[C:31]([C:47]([NH:49][NH:50][C:51]([C:53]2[CH:54]=[C:55]3[C:60](=[CH:61][CH:62]=2)[CH2:59][N:58]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:57][CH2:56]3)=[O:52])=O)=[N:32][C:33]([C:36]2[CH:41]=[CH:40][N:39]=[C:38]([C:42]([C:45]#[N:46])([CH3:44])[CH3:43])[CH:37]=2)=[CH:34][N:35]=1>ClCCl>[NH2:29][C:30]1[C:31]([C:47]2[O:52][C:51]([C:53]3[CH:54]=[C:55]4[C:60](=[CH:61][CH:62]=3)[CH2:59][N:58]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:57][CH2:56]4)=[N:50][N:49]=2)=[N:32][C:33]([C:36]2[CH:41]=[CH:40][N:39]=[C:38]([C:42]([C:45]#[N:46])([CH3:43])[CH3:44])[CH:37]=2)=[CH:34][N:35]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 70819338tert-butyl 6-[[[3-amino-6-[2-(1-cyano-1-methyl-ethyl)-4-pyridyl]pyrazine-2-carbonyl]amino]carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate

생성물 1

HCID 70856413tert-butyl 6-(5-(3-amino-6-(2-(2-cyanopropan-2-yl)pyridin-4-yl)pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

PS—PPh3 (145.6 mg, 0.3042 mmol) was suspended in dichloromethane (6.269 mL). Iodine (77.21 mg, 15.66 μL, 0.3042 mmol) was added and the mixture was stirred for 10 minutes before triethyl amine (63.10 mg, 86.91 μL, 0.6236 mmol) was added. After 5 minutes tert-butyl 6-[[[3-amino-6-[2-(1-cyano-1-methyl-ethyl)-4-pyridyl]pyrazine-2-carbonyl]amino]carbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylate (92 mg, 0.1521 mmol) was added as a solution in dichloromethane (3.919 mL) the mixture was stirred at ambient temperature for 1 hour. The resin was filtered off and the filtrate was washed with aqueous saturated sodium bicarbonate. The extracted organic phase was then dried over MgSO4 and concentrated in vacuo. The residue was taken onto the next step as is. (118.7 mg, assumed 100% yield). LC/MS m/z 539.2 [M+H]+.

후처리

  1. additionwas added
  2. filtrationThe resin was filtered off
  3. washthe filtrate was washed with aqueous saturated sodium bicarbonate
  4. dry with materialThe extracted organic phase was then dried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7fc349a745f741158199681eea686488
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877759B2

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