Ammonia → 6-(3-Ethylureido)-4-(phenylamino)nicotinamide

HRID 2174251ノート

反応式

HRID 2174251 の反応式
[NH:1]([C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:19])[NH:16][CH2:17][CH3:18])[N:11]=[CH:10][C:9]=1[C:20]([OH:22])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:26](CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.N>CN(C=O)C.CO.C(Cl)Cl>[CH2:17]([NH:16][C:15](=[O:19])[NH:14][C:12]1[CH:13]=[C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]([C:20]([NH2:26])=[O:22])=[CH:10][N:11]=1)[CH3:18]

参加物

7

反応物 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896500056-(3-Ethylureido)-4-(phenylamino)nicotinic acid

生成物 1

HCID 896503086-(3-Ethylureido)-4-(phenylamino)nicotinamide収率 8,918.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

4-anilino-6-(ethylcarbamoylamino)pyridine-3-carboxylic acid (i) (70 mg, 0.23 mmol) was suspended in DMF (2 mL) and N,N-diisopropylethyl amine (0.16 mL, 0.93 mmol) was added, causing the solid to dissolve. The [benzotriazol-1-yloxy(dimethylamino)methylene]-dimethyl-ammonium hexafluorophosphate (97 mg, 0.26 mmol) was added. After stirring at RT for 10 min, ammonia (1 mL, 25 mass %, 14.7 mmol) was added. The mixture was stirred overnight at RT. The mixture was quenched with NH4Cl and diluted with water and EtOAc. The mixture was extracted into EtOAc (3×20 mL), the organics combined and dried with brine then over MgSO4. The solvent was removed to afford a crude residue as a white solid. The solid was dissolved in MeOH/DCM and applied to a silica column, eluting with MeOH/DCM, to give Compound 6140 mg. 1H NMR (400 MHz, CD3OD) δ 8.46-8.39 (m, 1H), 7.44-7.37 (m, 2H), 7.29-7.23 (m, 2H), 7.22-7.14 (m, 1H), 6.84 (s, 1H), 3.29-3.24 (m, 2H), 1.18 (t, J=7.2 Hz, 3H).

後処理

  1. dissolutionto dissolve
  2. stirringThe mixture was stirred overnight at RT
  3. customThe mixture was quenched with NH4Cl
  4. additiondiluted with water and EtOAc
  5. extractionThe mixture was extracted into EtOAc (3×20 mL)
  6. dry with materialdried with brine
  7. customThe solvent was removed
  8. customto afford a crude residue as a white solid
  9. washeluting with MeOH/DCM

出典と根拠

ORDレコード
ord-fa5f338dde0544ae92d2783d63c17ac8
出典データセット
uspto-grants-2015_06
特許番号
US09060515B2

反応ノート

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