Triethylamine → 5-Bromo-3-[(3-morpholin-4-yl-propylamino)methyl]pyridin-2-ylamine

HRID 1362111

反応式

HRID 1362111 の反応式
Br.[NH2:2][C:3]1[C:8]([CH:9]=O)=[CH:7][C:6]([Br:11])=[CH:5][N:4]=1.C(N(CC)CC)C.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[BH4-].[Na+]>CO>[Br:11][C:6]1[CH:7]=[C:8]([CH2:9][NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:3]([NH2:2])=[N:4][CH:5]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 61055N-(3-Aminopropyl)morpholine2 回HCID 4311764Sodium borohydrideHCID 866061462-Amino-5-bromonicotinaldehyde hydrobromide

生成物 1

HCID 594569475-Bromo-3-[(3-morpholin-4-yl-propylamino)methyl]pyridin-2-ylamine収率 54%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2-amino-5-bromo-pyridine-3-carbaldehyde hydrobromide (4.30 g, 15.3 mmol) in MeOH (100 mL) was added triethylamine (4.3 mL, 31 mmol) and the mixture was stirred at room temperature for 10 min. The resulting suspension was treated with 4-(3-aminopropyl)morpholine (2.5 mL, 17 mmol) and the mixture was stirred for 7 h. TLC analysis indicated remaining starting material. Additional 4-(3-aminopropyl)morpholine (1.0 mL, 6.8 mmol) was added, and the mixture was allowed to stir overnight at room temperature. The mixture was cooled and then NaBH4 (0.87 g, 23.0 mmol) was added in two portions. The mixture was stirred at room temperature for 4 h. The solvent was removed in vacuo. Purification by column chromatography (silica gel, CH2Cl2/MeOH/Et3N, 97/2.5/0.5 to 85/14.5/0.5) gave the title compound (2.70 g, 54%) as a brown oil: MS (ESI) m/e 329 (M+H)+.

後処理

  1. stirringthe mixture was stirred for 7 h
  2. stirringto stir overnight at room temperature
  3. temperatureThe mixture was cooled
  4. stirringThe mixture was stirred at room temperature for 4 h
  5. customThe solvent was removed in vacuo
  6. customPurification by column chromatography (silica gel, CH2Cl2/MeOH/Et3N, 97/2.5/0.5 to 85/14.5/0.5)

出典と根拠

ORDレコード
ord-1631858270a5415c8ff9059ae98f209b
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

関連ノート

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