5-Methoxyindole-2-carboxylic acid → HCID 10789023, compound

Participants

Role	Name	HCID	Charge
Reactant	5-Methoxyindole-2-carboxylic acid	HCID 20401	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	3-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole	HCID 15380413	—
Reactant	Diisopropylether ethyl acetate	HCID 22281796	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	HCID 10789023	HCID 10789023	76%

Reaction Steps

Deprotection of 13 (260 mg, 0.72 mmol) as in Example C, and reaction with 5-methoxyindole-2-carboxylic acid (145 mg, 0.76 mmol) and EDCI.HCl (344 mg, 1.80 mmol) in DMA (3 mL) gave 14d (237 mg, 76%), mp (2×EtOAc/iPr2O) 241-243° C. 1H NMR [(CD3)2SO] δ 11.73 (d, J=1.3 Hz, 1 H, NH), 9.16 (s, 1 H, H-4), 8.35 (dd, J=7.2, 2.5 Hz, 1 H, H-6), 8.23 (dd, J=6.9, 2.4 Hz, 1 H, H-9), 7.79-7.70 (m, 2 H, H-7,8), 7.42 (d, J=8.9 Hz, 1 H, H-7'), 7.20 (d, J=1.9 Hz, 1 H, H-3'), 7.17 (d, J=2.4 Hz, 1 H, H-4'), 6.94 (dd, J=9.0, 2.4 Hz, 1 H, H-6'), 4.93 (dd, J=10.6, 9.2 Hz, 1 H, H-2), 4.70 (dd, J=10.9, 2.4 Hz, 1 H, H-2), 4.65-4.57 (m, 1 H, H-1), 4.18-4.07 (m, 2 H, CH2Cl), 3.79 (s, 3 H, OCH3).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06130237
Source dataset	uspto-grants-2000_10
ORD ID	ord-132c6e69d69848a38854b6a4747c7043
Source note	uspto-grants-2000_10