Cyclopropanemethanamine → N-Cyclopropylmethyl-4-fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzamide

HRID 1985765

反応式

HRID 1985765 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[NH:11][CH2:12][C:13]1[S:17][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:15][CH:14]=1.[CH:25]1([CH2:28][NH2:29])[CH2:27][CH2:26]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH:25]1([CH2:28][NH:29][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[C:3]([NH:11][CH2:12][C:13]3[S:17][C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[N:15][CH:14]=3)[CH:4]=2)[CH2:27][CH2:26]1

参加物

6

反応物 3

HCID 75646CyclopropanemethanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 220190564-Fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzoic acid

生成物 1

HCID 22019088N-Cyclopropylmethyl-4-fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzamide収率 83%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-fluoro-3-{[2-(pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-benzoic acid (35 mg, 0.10 mmol) in DMF (1 mL) at RT, cyclopropylmethyl amine (14 mg 0.20 mmol) was added followed by the addition of BOP reagent (53 mg, 0.12 mmol). The above reaction mixture was stirred for 2 h, diluted with EtOAc (10 mL), washed with 10% NaHCO3 (3×5 mL), and 10% LiCl (5 mL). The organic layer was dried over Na2SO4, concentrated and the residue was purified by preparative HPLC to give the title compound as a off-white solid (33 mg, 83%). (M+H)+=398.

後処理

  1. customThe above reaction mixture
  2. washwashed with 10% NaHCO3 (3×5 mL), and 10% LiCl (5 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-e09720abf955427e97a6c050b57cfffe
出典データセット
uspto-grants-2009_06
特許番号
US07547711B2

関連ノート

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