3-Chlorophenylacetic acid → 5-{1-[(3-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1909968노트

반응식

HRID 1909968 반응식
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:19]4[C:18]([NH2:20])=[N:17][CH:16]=[N:15][C:14]=4[N:13]([CH3:21])[CH:12]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](O)=[O:31])[CH:26]=[CH:27][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.CCOC(C)=O>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30]([N:2]2[C:10]3[C:5](=[CH:6][C:7]([C:11]4[C:19]5[C:18]([NH2:20])=[N:17][CH:16]=[N:15][C:14]=5[N:13]([CH3:21])[CH:12]=4)=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)=[O:31])[CH:26]=[CH:27][CH:28]=1

참가 물질

8

반응물 4

HCID 158793-Chlorophenylacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668238195-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine HCl

생성물 1

HCID 534694495-{1-[(3-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

시약·촉매·용매 3

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

In a 20 mL vial with cap, to the solution of 5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine HCl (70.6 mg, 0.234 mmol), (3-chlorophenyl)acetic acid (39.9 mg, 0.234 mmol), HATU (89 mg, 0.234 mmol) in DMF (2 mL) was added Hunig's base (0.163 mL, 0.936 mmol). The mixture was stirred at room temperature for overnight. LCMS showed reaction was completed. The reaction was poured into water (100 mL), purple solid formed. EtOAc (100 mL) was used to extract the product. The Organic phase was separated from the water phase, dried by MgSO4, evaporated to dryness, to give purple solid which still had some starting material. The solid was sonicated in water (10 mL), then filtered and dried to afford 5-{1-[(3-chlorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine as a purple solid.

후처리

  1. customreaction
  2. customformed
  3. extractionto extract the product
  4. customThe Organic phase was separated from the water phase
  5. dry with materialdried by MgSO4
  6. customevaporated to dryness
  7. customto give purple solid which
  8. filtrationfiltered
  9. customdried

출처 및 근거

ORD 기록
ord-75f6b79350cd4e9d97464176d43a6014
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598156B2

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