Triethylamine → HCID 71715063, compound

HRID 2206517Notes

Reaction equation

HRID 2206517 reaction equation
[CH3:1][C:2]1[N:3]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[N:19][CH:20]=2)[C:4]2[C:9]([C:10]=1[C:11]([OH:13])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.C1C=C2N=NN(O)C2=CC=1.N.C(N(CC)CC)C.[NH2:39][CH2:40][C:41]1[C:42]([OH:49])=[N:43][C:44]([CH3:48])=[CH:45][C:46]=1[CH3:47]>ClCCl>[CH3:47][C:46]1[CH:45]=[C:44]([CH3:48])[NH:43][C:42](=[O:49])[C:41]=1[CH2:40][NH:39][C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:14][C:15]2[CH:20]=[N:19][CH:18]=[N:17][CH:16]=2)[C:2]=1[CH3:1])=[O:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1131751H-Benzotriazol-1-ol--ammonia (1/1)HCID 117778681HCID 117778681, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 71715063HCID 71715063, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methyl-1-(pyrimidin-5-ylmethyl)-1H-indole-3-carboxylic acid (60 mg, 0.22 mmol), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (65 mg, 0.34 mmol), N-hydroxybenzotrizole (180 mg, 1.33 mmol) and triethylamine (46 mg, 0.34 mmol) in dichloromethane (30 mL) was stirred for 30 minutes at room temperature. Then to the mixture, 3-(aminomethyl)-4,6-dimethyl pyridin-2-ol (33.44 mg, 0.22 mmol) was added. The resultant mixture was stirred at room temperature for 12 hours. Then the mixture was washed with water (20 mL×3). The organic layer was concentrated to give a residue which was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(pyrimidin-5-ylmethyl)-1H-indole-3-carboxamide (17 mg, 19%). LRMS (M+H+) m/z: calcd 401.19. found 401. HPLC purity (214 nm): 92%. 1H. NMR (300 MHz, CD3OD): δ 9.03 (s, 1H), 8.43 (s, 2H), 7.80-7.78 (m, 1H), 7.39-7.36 (m, 1H), 7.19-7.16 (m, 2H), 5.56 (s, 2H), 4.55 (s, 2H), 2.62 (s, 3H), 2.42 (s, 3H), 2.45 (s, 3H).

Workup

  1. washThen the mixture was washed with water (20 mL×3)
  2. concentrationThe organic layer was concentrated
  3. customto give a residue which
  4. customwas purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-df2e9e97c6ea4b3096bb37743cd6b134
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

Loading…