HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → HCID 10181383, compound

HRID 966476
Notes
Print preview

Reaction equation

HRID 966476 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22]Cl)[CH:18]=2)[NH:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][C:26]1([CH3:33])[C:30]([CH3:32])([CH3:31])[CH2:29][NH:28][CH2:27]1.Cl>C(#N)C.C(Cl)Cl>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][N:28]3[CH2:29][C:30]([CH3:32])([CH3:31])[C:26]([CH3:33])([CH3:25])[CH2:27]3)[CH:18]=2)[NH:13][C:12]=1[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 223118013,3,4,4-TetramethylpyrrolidineHCID 23393871HCID 23393871, compound

Product 1

HCID 10181383HCID 10181383, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

A mixture of 5-(2-chloro-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (Example 1, Step A, 0.300 g, 0.873 mmol), 3,3,4,4-tetramethyl-pyrrolidine; hydrochloride (0.571 g, 3.49 mmol), K2CO2 (0.724 g, 5.234 mmol), and KI (0.014 g, 0.087 mmol) in 17.5 mL of acetonitrile was heated at reflux for 24 hours. The reaction mixture was cooled to room temperature, diluted with CH2Cl2 (50 mL) and washed with water (2×20 mL). The organic layer was dried over MgSO4 and concentrated to give 0.379 g (42.0%) of a white solid: mp 181-182° C.;IR(KBr)3283, 2961, 1671, 1652, 1457, 1171, 1074 cm−1; 1HNMR (400 MHz, DMSO-d6) δ 0.85 (s, 12H, NCH2C(CH3)2), 2.46 (s, 3H, CCH3), 2.60 (s, 4H, NCH2C(CH3)2), 2.81-2.84 (m, 2H, OCH2CH2),3.83 (t, J=6.12 Hz, 2H, OCH2CH2), 5.27 (s, 2H, OCH2Ar), 6.67 (dd, J=8.31, 3.20 Hz, 1H, ArH), 7.20 (d, J=8.40 Hz, 1H, ArH), 7.23-7.40 (m, 4H, ArH), 7.46 (d, J=7.89 Hz, 2H, ArH), 11.70 (s, 1H, NH); MS(APCI+): m/z 435.3 (MH+). Anal. Calcd for C27H34N2O3: C, 74.62; H, 7.89; N, 6.45. Found: C, 74.31; H, 7.98; N, 6.19.

Workup

  1. temperatureat reflux for 24 hours
  2. washwashed with water (2×20 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a98e2c1838084f62b492a519c5e49c32
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951848B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes