Triethylamine → HCID 44177406, 화합물

HRID 1091879노트

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HRID 1091879 반응식
[CH2:1]([N:8]1[CH2:23][CH2:22][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][C:16]([C:19](O)=[O:20])=[CH:17][C:18]=3[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[NH2:50][CH:51]1[CH2:56][CH2:55][N:54]([CH2:57][C:58]2[CH:63]=[CH:62][C:61]([C:64]#[N:65])=[CH:60][CH:59]=2)[CH2:53][CH2:52]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:1]([N:8]1[CH2:23][CH2:22][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]([NH:50][CH:51]4[CH2:56][CH2:55][N:54]([CH2:57][C:58]5[CH:63]=[CH:62][C:61]([C:64]#[N:65])=[CH:60][CH:59]=5)[CH2:53][CH2:52]4)=[O:20])=[CH:17][C:18]=3[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21231111HCID 21231111, 화합물HCID 44120478HCID 44120478, 화합물

생성물 1

HCID 44177406HCID 44177406, 화합물수율 97%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid (50 mg, 0.2 mmol) in DMF (2 mL), HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (75 mg, 0.2 mmol), 4-amino-1-(4-cyanobenzyl)piperidine dihydrochloride (47 mg, 0.2 mmol) and triethylamine (105 μL, 76 mg, 0.8 mmol) were added. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into saturated sodium bicarbonate solution (30 mL) to give a white precipitate which was filtered and dried under vacuuo. The resulting solid was triturated with ethyl ether to yield Compound 4 as a white crystalline solid (80 mg, 97%). 1H NMR (DMSO-d6): δ 11.00 (1H, br s); 8.00 (1H, d, J=7.7 Hz); 7.82 (1H, s); 7.78 (2H, d, J=8.3 Hz); 7.53 (1H, d, J=11.8 Hz); 7.50 (2H, d, J=7.7 Hz); 7.39 (2H, d, J=6.6 Hz); 7.36 (2H, d, J=8.3 Hz); 7.32-7.23 (2H, m); 3.76 (3H, br s); 3.58 (4H, d, J=10.5 Hz); 2.89-2.73 (6H, m); 2.06 (2H, t, J=11.0 Hz); 1.76 (2H, d, J=9.9 Hz); 1.58 (2H, q, J=10.7 Hz). MS (M+H)+=504.

후처리

  1. customThe resulting reaction mixture
  2. customto give a white precipitate which
  3. filtrationwas filtered
  4. customdried under vacuuo
  5. customThe resulting solid was triturated with ethyl ether

출처 및 근거

ORD 기록
ord-e7e781594b2e4f868b78952dd8570172
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129390B2

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