Triethylamine → HCID 136163781, compound

HRID 44234Notes

Reaction equation

HRID 44234 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[C:14]4[CH:26]=[CH:25][CH:24]=[N:23][C:15]=4[NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:12]3=[N:11][N:10]=2)=[CH:5][CH:4]=1.[NH:27]1[CH2:32][CH2:31][CH:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:29][CH2:28]1.C(N(CC)CC)C>CC(N(C)C)=O.O>[N:11]1[N:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][N:27]3[CH2:28][CH2:29][CH:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:31][CH2:32]3)=[CH:8][CH:7]=2)[N:13]2[C:12]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[NH:16][C:15]1[N:23]=[CH:24][CH:25]=[CH:26][C:14]2=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 136084722HCID 136084722, compound

Product 1

HCID 136163781HCID 136163781, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 3-(4-(chloromethyl)phenyl)-9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepine (1.3 g, 3.62 mmol), tert-butyl piperidin-4-ylcarbamate (0.71 g, 3.80 mmol), triethylamine (1 mL) in dimethylacetamide (15 mL) was stirred at 75° C. for 20 hours. The mixture wass diluted with water (30 mL). The resulting suspension was stirred at room temperature. The solid was collected by filtration, washed thoroughly with water and dried under high vacuum. The tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzyl)piperidin-4-yl)carbamate was obtained as a yellow solid (1.3 g, 69%). M.p.=145-147° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.76 (s, 1H), 8.18 (dd, J=4.4, 1.2 Hz, 1H), 7.93 (dd, J=8.0, 1.2 Hz, 1H), 7.41 (td, J=8.0, 1.6 Hz, 1H), 7.35-7.30 (m, 5H), 7.15-7.08 (m, 2H), 6.87 (dd, J=8.0, 4.8 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 3.45 (s, 2H), 3.21-3.06 (m, 1H), 2.80-2.65 (m, 2H), 2.0-1.9 (m, 2H), 1.7-1.6 (m, 2H), 1.4-1.3 (m, 2H), 1.34 (s, 9H); LCMS [M+H]: 524.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed thoroughly with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-196da8864db146e09811b8ed61812592
Source dataset
uspto-grants-2013_09
Patent number
US08541407B2

Reaction notes

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