1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (R)-1-(3-(Ethoxycarbonyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 2099839Notes

Reaction equation

HRID 2099839 reaction equation
[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:9]=2)[CH:5]=[C:4]([CH2:19][C@@H:20]([O:24][C:25]([N:27]2[CH2:32][CH2:31][CH:30]([C:33]3[C:34](=[O:43])[NH:35][C:36]4[C:41]([CH:42]=3)=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:29][CH2:28]2)=[O:26])[C:21](O)=[O:22])[CH:3]=1.[NH2:44][C:45](=[N:51]O)[C:46]([O:48][CH2:49][CH3:50])=[O:47].Cl.CN(C)CCCN=C=NCC>COCCOCCOC>[O:43]=[C:34]1[C:33]([CH:30]2[CH2:29][CH2:28][N:27]([C:25]([O:24][C@@H:20]([C:21]3[O:22][N:51]=[C:45]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[N:44]=3)[CH2:19][C:4]3[CH:3]=[C:2]([CH3:1])[C:10]4[C:6](=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[N:9]=4)[CH:5]=3)=[O:26])[CH2:32][CH2:31]2)=[CH:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35]1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetateHCID 57794582HCID 57794582, compound

Product 1

HCID 57794676(R)-1-(3-(Ethoxycarbonyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylateYield 34%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A stirred solution of (R)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carbonyloxy)propanoic acid (28.5 mg, 0.0471 mmol) in anhydrous diglyme (2.5 mL) was treated with ethyl 2-amino-2-(hydroxyimino)acetate (6.54 mg, 0.0495 mmol) and 1-[3-(dimethylamino)propyl]3-ethylcarbodiimide hydrochloride (0.49 mg, 0.0495 mmol) at room temperature. The mixture was stirred overnight at room temperature and then overnight at 110° C. After cooling to room temperature and removal of the solvent in vacuo, the crude compound was purified using preparative HPLC to afford a tan gum (11.2 mg, 34%). 1H-NMR (CDCl3, 400 MHz) δ 8.0 (s,1H), 7.58 (s, 1H), 7.57 (s, 1H), 7.46 (m, 1H), 7.30 (s,1H), 7.24-7.20 (m, 2H), 6.93 (s,1H), 6.17-6.15 (m, 1H), 5.71 (s, 2H), 4.50-4.48 (m, 2H), 4.29-4.20 (m, 2H), 3.65-3.55 (m, 2H), 3.40-3.38 (m, 2H), 3.20-2.81 (m, 4H), 2.59 (s, 3 h), 2.03-1.72 (m, 4H), 1.44-1.38 (m, 3H), 0.95-0.86 (m, 2H), −0.045 (s, 9H).

Workup

  1. customovernight
  2. customat 110° C
  3. temperatureAfter cooling to room temperature
  4. customremoval of the solvent in vacuo
  5. customthe crude compound was purified

Sources & evidence

ORD record
ord-095aae7ce4cc48f5a4eba8a74e8bafc1
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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