4-Methylmorpholine → 6-[(4-Chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester

HRID 389621ノート

反応式

HRID 389621 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](O)=[O:9])[CH:3]=1.[NH2:11][C:12]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH3:21][O:20][C:18]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:11][C:8]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=2)=[O:9])[N:17]=1)=[O:19]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 2308904-Chloropyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 13809143Methyl 6-aminopyridine-2-carboxylate

生成物 1

HCID 668487256-[(4-Chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-chloro-pyridine-2-carboxylic acid (16.3 g, 103 mmol), methyl 6-aminopicolinate (3.0 g, 18.6 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 41.1 g, 108 mmol), and N-methyl morpholine (12.5 mL, 108 mmol) in N,N-dimethylformamide was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure, and the residue suspended in acetonitrile. The solid thus obtained was isolated by filtration, washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL) and dried under reduced pressure to afford 6-[(4-chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester as a white powder (25.6, 93% yield).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customThe solid thus obtained
  3. customwas isolated by filtration
  4. washwashed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL)
  5. customdried under reduced pressure

出典と根拠

ORDレコード
ord-3b2cab38540d4b4b9e051fbf3c192cb0
出典データセット
uspto-grants-2013_02
特許番号
US08378108B2

反応ノート

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