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Ammonia → 8-Amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid amide

HRID 222132
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HRID 222132 반응식
[NH2:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3[C:14]([C:15](O)=[O:16])=[CH:13][N:12]([CH3:18])[C:9]=32)=[CH:4][N:3]=1.C1C=CC2N(O)N=[N:25]C=2C=1.N.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3[C:14]([C:15]([NH2:25])=[O:16])=[CH:13][N:12]([CH3:18])[C:9]=32)=[CH:4][N:3]=1
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참가 물질

7

반응물 5

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 687043988-Amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid

생성물 1

HCID 68704357
8-Amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid amide
수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 8-amino-1-methyl-4,5-dihydro-1H-1,7,9-triaza -cyclopenta[a]naphthalene-3-carboxylic acid M2 (0.08 mmol) in dry DMF (4 mL), HOBT.NH3 (0.164 mmol), TBTU (0.164 mmol) and DIEA (0.328 mmol) were added. The mixture was stirred at rt for 24 h then the solvent was evaporated. The residue was suspended in 10 mL of water, filtered, washed with water and dried in vacuo, providing the title compound (55% yield). ESI (+) MS: m/z 244 (MH+). 1H NMR: 2.73 (t, J=7.44, 2H), 3.00 (t, J=7.44, 2H), 4.04 (s, 3H), 6.94 (bs, 1H), 7.35 (bs, 1H), 7.73 (s, 1H), 7.96 (s, 1H), 7.76 (bs, 3H).

후처리

  1. customthe solvent was evaporated
  2. filtrationfiltered
  3. washwashed with water
  4. customdried in vacuo

출처 및 근거

ORD 기록
ord-aad019abf8a24bbe8c1a8934bb897253
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207180B2

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