Triethylamine → Isopropyl-carbamic acid 1-[2,3-dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-cyclopropylmethyl ester

HRID 2171021Notes

Reaction equation

HRID 2171021 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][O:7][C:8]2[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH2:20][CH2:21][C:22]3=[O:27])[CH2:5][CH2:4]1.C(N(CC)CC)C.[N:35]([CH:38]([CH3:40])[CH3:39])=[C:36]=[O:37].COC1C(OC)=CC=C(C2C=CC=C3C=2CCC3=O)C=1OCC1(COC(=O)NCC)CC1>ClCCl>[CH3:15][O:14][C:13]1[C:12]([O:16][CH3:17])=[CH:11][CH:10]=[C:9]([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH2:20][CH2:21][C:22]3=[O:27])[C:8]=1[O:7][CH2:6][C:3]1([CH2:2][O:1][C:36](=[O:37])[NH:35][CH:38]([CH3:40])[CH3:39])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 545762924-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one2×HCID 71279321Ethyl-carbamic acid 1-[2,3-dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-cyclopropylmethyl ester

Product 1

HCID 54577165Isopropyl-carbamic acid 1-[2,3-dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-cyclopropylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 177) (200 mg, 0.543 mmol) in dichloromethane (20 mL), were added triethylamine (164 mg, 1.623 mmol) and 2-isocyanatopropane (184 mg, 2.164 mmol) and the resultant reaction mixture was subjected to the conditions used in the preparation of Compound 179 to afford the title compound as a solid.

Workup

  1. customthe resultant reaction mixture

Sources & evidence

ORD record
ord-bb1dd4263d0e450ebc285bba8ad06d33
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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