Triethylamine → HCID 58826320, compound

HRID 1172366Notes

Reaction equation

HRID 1172366 reaction equation
Cl.[NH2:2][C@H:3]([CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([CH3:18])[CH:17]=1)[NH:14][N:13]=[CH:12]2)[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:21](=[O:22])C1.C(N(CC)CC)C.[NH:44]1[CH2:49][CH2:48][CH:47]([C:50]2[C:51](=[O:60])[NH:52][C:53]3[C:58]([CH:59]=2)=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH2:46][CH2:45]1>CN(C=O)C.C(Cl)Cl>[CH3:18][C:16]1[CH:17]=[C:9]([CH2:8][C@@H:3]([NH:2][C:21]([N:44]2[CH2:45][CH2:46][CH:47]([C:50]3[C:51](=[O:60])[NH:52][C:53]4[C:58]([CH:59]=3)=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH2:48][CH2:49]2)=[O:22])[C:4]([O:6][CH3:7])=[O:5])[CH:10]=[C:11]2[C:15]=1[NH:14][N:13]=[CH:12]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 183210463-(Piperidin-4-yl)quinolin-2(1H)-oneHCID 66603772HCID 66603772, compound

Product 1

HCID 58826320HCID 58826320, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-methyl 2-amino-3-(7-methyl-1H-indazol-5-yl)propanoate hydrochloride (2.69 g, 10 mmol) in DMF (20 mL) was added N,N′-disuccinimidyl carbonate followed by triethylamine (5.6 mL, 40 mmol). After 20 min, 3-(piperidin-4-yl)quinolin-2(1H)-one (2.28 g, 10 mmol) was added at once. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was then diluted with CH2Cl2 (250 mL), washed with water (2×100 mL), 1 M sodium hydroxide (30 mL) and then with 1.0 M hydrogen chloride (100 mL). The organic phase was dried (Na2SO4) and then purified by flash chromatography using 5% methanol in dichloromethane to give (R)-methyl 3-(7-methyl-1H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamido)propanoate in 68% yield. MS (ESI) 488 (M+H) ; Rf=2.14.

Workup

  1. washwashed with water (2×100 mL), 1 M sodium hydroxide (30 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c85004a847fe4e66b404e4890f3f681f
Source dataset
uspto-grants-2010_11
Patent number
US07834007B2

Reaction notes

Loading…