Ammonium Chloride → HCID 178492246, 화합물

HRID 1876223노트

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HRID 1876223 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178492246HCID 178492246, 화합물수율 13.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

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]+)).

후처리

  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

출처 및 근거

ORD 기록
ord-ebc8b57ccaa942dc83c394b54bc5b79a
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309562B2

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