Triethylamine → {3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-carbamic acid ethyl ester

HRID 2171041Notes

Reaction equation

HRID 2171041 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:10]=2[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH2:22][C:23]3=[O:28])[CH2:6][O:5][CH2:4]1.C(N(CC)CC)C.[C:36](Cl)(=[O:40])[O:37][CH2:38][CH3:39].COC1C(OC)=CC=C(C2C=CC=C3C=2CCC3=O)C=1OCC1(CNC(=O)C)COC1>ClCCl>[CH2:38]([O:37][C:36](=[O:40])[NH:1][CH2:2][C:3]1([CH2:7][O:8][C:9]2[C:10]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH2:21][CH2:22][C:23]4=[O:28])=[CH:11][CH:12]=[C:13]([O:17][CH3:18])[C:14]=2[O:15][CH3:16])[CH2:4][O:5][CH2:6]1)[CH3:39]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 54577376N-{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-acetamideHCID 674679514-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one2×

Product 1

HCID 67466390{3-[2,3-Dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-oxetan-3-ylmethyl}-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-[2-(3-Aminomethyl-oxetan-3-ylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 191) (150 mg, 0.3916 mmol) in dichloromethane (15 mL), were added triethylamine (118 mg, 1.174 mmol) and ethyl carbonochloridate (84 mg, 0.783 mmol) and the resultant reaction mixture was subjected to the conditions used in the preparation of Compound 192 to afford the title compound as a solid.

Workup

  1. customthe resultant reaction mixture

Sources & evidence

ORD record
ord-f8ba3360d55b4b62a8c8803bd304dcf7
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…