Triethylsilane → N-cyclopropyl-2,4-difluoro-5-((2-(pyridin-2-ylamino)thiazol-5-yl)methylamino)benzamide

HRID 6876

반응식

HRID 6876 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH:13]=O)=[CH:11][N:12]=1.[NH2:15][C:16]1[C:17]([F:29])=[CH:18][C:19]([F:28])=[C:20]([CH:27]=1)[C:21]([NH:23][CH:24]1[CH2:26][CH2:25]1)=[O:22].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH:24]1([NH:23][C:21](=[O:22])[C:20]2[CH:27]=[C:16]([NH:15][CH2:13][C:10]3[S:9][C:8]([NH:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:12][CH:11]=3)[C:17]([F:29])=[CH:18][C:19]=2[F:28])[CH2:25][CH2:26]1

참가 물질

5

반응물 3

HCID 12052TriethylsilaneHCID 219665075-amino-N-cyclopropyl-2,4-difluorobenzamideHCID 220190582-(Pyridin-2-ylamino)thiazole-5-carbaldehyde

생성물 1

HCID 11632737N-cyclopropyl-2,4-difluoro-5-((2-(pyridin-2-ylamino)thiazol-5-yl)methylamino)benzamide수율 47.3%

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

A mixture of 2-[pyridin-2-ylamino]-thiazole-5-carbaldehyde (41.0 mg, 0.2 mmol) and 5-amino-N-cyclopropyl-2,4-difluorobenzamide (46.6 mg, 0.22 mmol) in TFA/DCM (1:1, 1 mL) was stirred at RT for 10 min and triethylsilane (0.1 mL) was added. The mixture was stirred for 1 h, then concentrated and the residue was neutralized with NaHCO3 solution and the precipitates occurred. The precipitates were collected, washed with water and dried. The solid was triturated with MeOH and filtered to afford the title compound as a grayish solid (38 mg, 47%). Small amount of solid was boiled in methanol, the mixture was cooled to RT and filtered to afford a white solid. MS m/z 402 (M+H)+. 1H NMR (DMSO-d6) δ 8.23 (d, 1H, J=4.0 Hz), 8.15 (s, 1 H), 7.65 (t, 1 H, J=7.15 Hz), 7.26 (s, 1 H), 7.16 (m, 1 H), 7.01 (d, 1 H, J=8.75 Hz), 6.95 (m, 1 H), 6.89 (t, 1 H, J=7.15 Hz), 6.12 (s 1 H), 4.43 (m, 2 H), 2.79 (m, 1 H), 0.69 (m, 2 H), 0.51 (m, 2 H).

후처리

  1. stirringThe mixture was stirred for 1 h
  2. concentrationconcentrated
  3. customThe precipitates were collected
  4. washwashed with water
  5. customdried
  6. customThe solid was triturated with MeOH
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-c09aa937df8b486caaee08ce9bc04f1a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084160B2

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