Methylamine → [1,1-dimethyl-2-(7-methylcarbamoylmethoxy-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 1272224Notes

Reaction equation

HRID 1272224 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:26])([CH3:25])[CH2:10][C:11]1[C:19]2[C:14](=[C:15]([O:20][CH2:21][C:22](O)=[O:23])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][NH2:28]>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([CH3:25])([CH3:26])[CH2:10][C:11]1[C:19]2[C:14](=[C:15]([O:20][CH2:21][C:22](=[O:23])[NH:28][CH3:27])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22014777[3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yloxy]acetic acid

Product 1

HCID 69517962[1,1-dimethyl-2-(7-methylcarbamoylmethoxy-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl esterYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [3-(2-tert-butoxycarbonylamino-2-methyl-propyl)-1H-indol-7-yloxy]acetic acid (480 mg, 1.32 mmol) in dimethylformamide (5.0 mL) is added methyl amine (1.52 mL, 1.0 M in tetrahydrofuran, 1.52 mmol) and Bop reagents (670 mg, 1.52 mmol). The reaction mixture is stirred at room temperature for 3 hours before evaporation to dryness. The resulting residue is chromatographed (30% ethyl acetate/hexane) to give 500 mg of [1,1-dimethyl-2-(7-methylcarbamoylmethoxy-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (75%). FDMS m/e=375.1 (M++1).

Workup

  1. customThe resulting residue is chromatographed (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eb7a250c5b7d48349f5be51252e4f12f
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

Loading…