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

HRID 6876

反応式

HRID 6876 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c09aa937df8b486caaee08ce9bc04f1a
出典データセット
uspto-grants-2006_08
特許番号
US07084160B2

関連ノート

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