Diisopropylethylamine → HCID 58790370, 화합물

HRID 418620

반응식

HRID 418620 반응식
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][C:4](O)=[O:5].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[Cl:29][CH2:30][CH2:31][N:32]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[S:49][C:48]3[C:43](=[N:44][CH:45]=[CH:46][C:47]=3[O:50][C:51]3[CH:56]=[CH:55][C:54]([NH2:57])=[CH:53][C:52]=3[F:58])[CH:42]=2)=[CH:37][CH:36]=1)[CH3:33].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:29][CH2:30][CH2:31][N:32]([CH2:34][C:35]1[CH:36]=[CH:37][C:38]([C:41]2[S:49][C:48]3[C:43](=[N:44][CH:45]=[CH:46][C:47]=3[O:50][C:51]3[CH:56]=[CH:55][C:54]([NH:57][C:4](=[O:5])[CH2:3][C:2]([NH:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)=[O:1])=[CH:53][C:52]=3[F:58])[CH:42]=2)=[CH:39][CH:40]=1)[CH3:33]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2565932-(Phenylcarbamoyl)acetic acidHCID 587901534-(2-(4-(((2-Chloroethyl)(methyl)amino)methyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

생성물 1

HCID 58790370HCID 58790370, 화합물수율 21.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of the acid 1 (142 mg, 2 eq, 1.58 mmol) in dry DCM (10 ml), at 0° C., was added, BOPCl (502 mg, 2 eq, 0.826 mmol) and the reaction mixture was stirred for 10 minutes. A solution of the amine 87 (348 mg, 0.79 mmol) and iPr2NEt (610 mg, 6 eq, 4.72 mmol) in dry DCM (7 ml) was then added and the reaction mixture was stirred at RT overnight. The reaction mixture was concentrated to dryness and partitioned between EtOAc and satd NaHCO3 soln, the organic phase was washed twice with saturated NaHCO3 then collected, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was purified by column chromatography (EtOAc) to afford the desired product 88 as an off-white solid (102 mg, 21% yield). 1H NMR (DMSO-d6) δ (ppm): 10.58 (s, 1H), 10.22 (s, 1H), 8.48 (d, J=5.28 Hz, 1H), 8.03 (s, 1H), 7.85 (m, 3H), 7.59 (m, 2H), 7.43 (m, 4H), 7.32 (m, 2H), 7.05 (t, J=7.43 Hz, 1H), 6.61 (m, 1H), 3.70 (t, J=6.65 Hz, 2H), 3.59 (s, 2H), 3.50 (s, 2H), 2.69 (m, 2H), 2.20 (s, 3H).

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between EtOAc
  3. washthe organic phase was washed twice with saturated NaHCO3
  4. customthen collected
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe crude was purified by column chromatography (EtOAc)

출처 및 근거

ORD 기록
ord-a69aefa54ee04f29984f45fe93d62569
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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