1-Hydroxybenzotriazole → HCID 68651458, 화합물

HRID 646675노트

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HRID 646675 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)=[N:6][C:7]=1[C:8]([NH:10][CH3:11])=[O:9].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:55][CH2:56][C:57]1[CH:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=1>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH3:11])=[O:9])=[N:6][C:5]([C:12]2[CH:20]=[CH:19][CH:18]=[C:14]([C:15]([NH:55][CH2:56][C:57]3[CH:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=3)=[O:17])[CH:13]=2)=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 4278144-AminobenzylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 587105713-{5-Amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzoic acid

생성물 1

HCID 68651458HCID 68651458, 화합물수율 39%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 3-{5-amino-6-[(methylamino)carbonyl]pyrazin-2-yl}benzoic acid (0.10 g, 0.37 mmol), HOBt (0.055 g, 0.41 mmol) and HBTU (0.15 g, 0.41 mmol) in DMF (1.2 mL) was stirred at r.t. for 10 min. A solution of [4-(aminomethyl)phenyl]amine (0.050 mL, 0.44 mmol) in DMF (1.0 mL) was added and the resulting solution was stirred for 12 h at r.t. The solution was concentrated in vacuo and the crude mixture was partitioned between EtOAc (100 mL) and brine (50 mL). The organic layer was washed with brine (2×50 mL) and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified via column chromatography (SiO2, 5% MeOH/CH2Cl2) and trituration of the product gave 0.035 g (39% yield) of product: 1H NMR (400 MHz, d6-DMSO): 8.95 (t, 1H), 8.91 (s, 1H), 8.84 (m, 1H), 8.50 (m, 1H), 8.37 (dt, 1H), 7.87 (dt, 1H), 7.56 (t, 1H), 7.01 (d, 2H), 6.52 (m, 2H), 4.97 (s, 2H), 4.35 (d, 2H), 2.85 (d, 3H); MS (EI) for C20H20N6O2: 377 (MH+).

후처리

  1. concentrationThe solution was concentrated in vacuo
  2. customthe crude mixture was partitioned between EtOAc (100 mL) and brine (50 mL)
  3. washThe organic layer was washed with brine (2×50 mL)
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via column chromatography (SiO2, 5% MeOH/CH2Cl2) and trituration of the product

출처 및 근거

ORD 기록
ord-d39a61c8f2f3457587b2df083079a5ad
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704995B2

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