Triethylamine → HCID 44177406、化合物

HRID 1042529ノート

反応式

HRID 1042529 の反応式
[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

参加物

7

反応物 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、化合物HCID 44120478HCID 44120478、化合物

生成物 1

HCID 44177406HCID 44177406、化合物収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-212dbd16f1ce4d18a8972bfe91c07f34
出典データセット
uspto-grants-2013_10
特許番号
US08557822B2

反応ノート

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