HCID 59612419, compound → [5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine

HRID 472529Notes

Reaction equation

HRID 472529 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([NH:19][C:20]3[N:37]=[C:23]4[CH:24]=[CH:25][CH:26]=[C:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[CH2:34][O:35][CH3:36])[N:22]4[N:21]=3)[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH3:36][O:35][CH2:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:27]1[N:22]2[N:21]=[C:20]([NH:19][C:16]3[CH:17]=[CH:18][C:11]4[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=4[CH:15]=3)[N:37]=[C:23]2[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 59612419HCID 59612419, compound

Product 1

HCID 59612550[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amineYield 94.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

7-[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester (105.0 mg, 0.210 mmol) was stirred in 3M trifluoroacetic acid in dichloromethane (10 mL) for 30 minutes. The volatiles were evaporated and the residue was dissolved in ethyl acetate and washed with sodium carbonate solution (2×) and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. Product isolated as a foam (0.079 g, 89%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.64 (d, J=7.7 Hz, 1H), 7.58-7.41 (m, 5H), 7.25-7.21 (m, 1H), 7.16-7.04 (m, 1H), 6.99 (d, J=8.0 Hz, 1H), 6.91-6.87 (m, 1H), 4.35 (br s, 2H), 3.20 (s, 3H), 2.98-2.81 (m, 8H), 2.02 (br s, 1H). MS=400 (MH)+.

Workup

  1. customThe volatiles were evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with sodium carbonate solution (2×) and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-475c8c0c14924c43885dd1e00efbdebe
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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