Ammonium Chloride → HCID 178492246、化合物

HRID 1876223ノート

反応式

HRID 1876223 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:22])[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([C:20]#[N:21])[N:11]=2)=[CH:5][CH:4]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:22])[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([C:20]3[NH:25][N:24]=[N:23][N:21]=3)[N:11]=2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 575165474-[(4-Methoxyphenyl)(methyl)amino]quinazoline-2-carbonitrile

生成物 1

HCID 178492246HCID 178492246、化合物収率 13.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

To 4-[(4-methoxy-phenyl)-methyl-amino]-quinazoline-2-carbonitrile (100 mg, 0.34 mmol) in DMF (3.4 mL) was added sodium azide (269 mg, 4.1 mmol) and ammonium chloride (220 mg, 4.1 mmol). The reaction was heated to 130° C. for 15 min in a microwave. The reaction was quenched with aqueous NaHCO3 and diluted with EtOAc. The aqueous phase was acidified with HCl (12 M) to pH 1 and extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated. Purification via gradient MPLC gave 15 mg (13%) of the title compound as a solid. 1H NMR (MeOH-d4) δ 7.91 (d, 1H), 7.74-7.70 (t, 1H), 7.30 (d, 2H), 7.16 (t, 1H), 7.06 (d, 2H), 7.0 (d, 1H), 3.86 (s, 3H), 3.82 (s, 3H); LC-MS (ESI+; 334 ([M+H]+)).

後処理

  1. customThe reaction was quenched with aqueous NaHCO3
  2. additiondiluted with EtOAc
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via gradient MPLC

出典と根拠

ORDレコード
ord-ebc8b57ccaa942dc83c394b54bc5b79a
出典データセット
uspto-grants-2012_11
特許番号
US08309562B2

反応ノート

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