Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 2-Amino-N-(5-bromo-thiophen-2-ylmethyl)-6-methoxymethyl-nicotinamide

HRID 2079976

反応式

HRID 2079976 の反応式
[Br:1][C:2]1[S:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.[NH2:9][C:10]1[N:18]=[C:17]([CH2:19][O:20][CH3:21])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[NH2:9][C:10]1[N:18]=[C:17]([CH2:19][O:20][CH3:21])[CH:16]=[CH:15][C:11]=1[C:12]([NH:8][CH2:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:13]

参加物

5

反応物 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 231304372-Amino-6-methoxymethylnicotinic acidHCID 23130577(5-Bromothiophen-2-yl)methanamine

生成物 1

HCID 231307182-Amino-N-(5-bromo-thiophen-2-ylmethyl)-6-methoxymethyl-nicotinamide収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of C-(5-bromo-thiophen-2-yl)-methylamine (250 mg, 1.3 mmol) in N,N-dimethylformamide (5 mL) were added tiethylamine (0.54 mL, 3.9 mmol), 2-amino-6-methoxymethyl-nicotinic acid (240 mg, 1.3 mmol) described in Preparation Example A-11, and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (690 mg, 1.6 mmol) sequentially on an ice bath, then, the solution was stirred for 2 days at room temperature. The reaction solution was partitioned in water and ethyl acetate. The organic layer was separated, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1), and the title compound (370 mg, 1.0 mmol, 79%) was obtained as a white solid.

後処理

  1. customThe reaction solution was partitioned in water
  2. customThe organic layer was separated
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-6bffc70267e44f669ec5e34632e48f31
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

関連ノート

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