Tetrafluoro-m-phenylenediamine dihydrochloride → Ammonium Hydroxide

Participants

Role	Name	HCID	Charge
Reactant	Tetrafluoro-m-phenylenediamine dihydrochloride	HCID 149026	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(2R)-2-(((tert-butoxy)carbonyl)amino)-2-cyclohexylacetic acid	HCID 7014890	—
Reactant	(R)-(Cyclohexyl-[2-(2-dimethylamino-ethylcarbamoyl)-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-ylcarbamoyl]-methyl)-carbamic Acid tert-butyl Ester	HCID 69746610	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Ammonium Hydroxide	HCID 14923	—
Product	(R)-(Cyclohexyl-[2-(2-dimethylamino-ethylcarbamoyl)-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-ylcarbamoyl]-methyl)-carbamic Acid tert-butyl Ester	HCID 69746610	—

Reaction Steps

Preparation of intermediate 228(a) from Intermediate 171(a) of Example 171 (200 mg, 0.571 mmol), (R)-tert-butoxycarbonylamino-cyclohexyl-acetic acid (147 mg, 0.571 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (131 mg, 0.686 mmol), and 4-dimethylaminopyridine (84 mg, 0.688 mmol) in N,N-dimethylformamide (8.0 mL) was carried out analogously to Example 190, step 2. When the reaction was judged complete, the volatile components were removed in vacuo, and the resulting residue was dissolved in methanol and loaded onto a silica gel plug. The plug was then loaded onto a silica gel column and eluted with 40:3:0.3 dichloromethane: methanol: ammonium hydroxide to afford Intermediate 228(a) (77 mg, 0.139 mmol) as a yellow solid in 24% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06967198B2
Source dataset	uspto-grants-2005_11
ORD ID	ord-66b3ae33364b44f496e82ede2e5bcc5d
Source note	uspto-grants-2005_11