Triethylamine → HCID 86690694, compound

HRID 711370Notes

Reaction equation

HRID 711370 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[CH:11][C:10]2[N:9]=[CH:8][C:7]3[N:13]=[N:14][N:15]([CH:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[C:6]=3[C:5]=2[N:4]=1.[C:22]([O:25][C@@H:26]([CH3:30])[C:27](Cl)=[O:28])(=[O:24])[CH3:23].CCN(CC)CC>C(Cl)Cl>[C:22]([O:25][C@@H:26]([CH3:30])[C:27]([N:19]1[CH2:20][CH2:21][CH:16]([N:15]2[C:6]3[C:5]4[N:4]=[C:3]([Cl:2])[CH:12]=[CH:11][C:10]=4[N:9]=[CH:8][C:7]=3[N:13]=[N:14]2)[CH2:17][CH2:18]1)=[O:28])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11094804(1S)-2-Chloro-1-methyl-2-oxoethyl acetateHCID 86690695HCID 86690695, compound

Product 1

HCID 86690694HCID 86690694, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-chloro-1-(piperidin-4-yl)-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridine hydrochloride (1 g, 3.08 mmol) in 10 mL of CH2Cl2 was added (S)-1-chloro-1-oxopropan-2-yl acetate (1.4 g, 9.23 mmol) and Et3N (2.2 mL). After the mixture was stirred at room temperature for 2 h, it was quenched with water (10 mL). The resulting mixture was extracted with CH2Cl2 (2×20 mL). The combined organic layer was dried over anhydrous Na2SO4, and then was concentrated in vacuo to afford the (S)-1-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-1-oxopropan-2-yl acetate (1.2 g). MS (m/z): 403 (M+H)+.

Workup

  1. customit was quenched with water (10 mL)
  2. extractionThe resulting mixture was extracted with CH2Cl2 (2×20 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-ce15fe1b8f5844bd90eeeee05f1cd301
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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