(S)-2-Trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine → (R)-10-(3-Phenoxymethyl-piperazin-1-yl)-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Participants

Role	Name	HCID	Charge
Reactant	(S)-2-Trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine	HCID 10250638	—
Reactant	HCID 69214041	HCID 69214041	—
Reactant	10H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)	HCID 135525650	—
Product	(R)-10-(3-Phenoxymethyl-piperazin-1-yl)-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene	HCID 135546110	39.9%

Reaction Steps

By using a method similr to the coupling method for (S)-2-trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine, 2-methyl-4H-3-thia-4,9-diaza-benzo[f]-azulen-10-ylamine hydrochloride (1.2 g) and (R)-2-phenoxymethyl-piperazine (2.6 g) gives the title compound as a yellow solid (728 mg): mp=64-81° C.: 1H NMR (CDCl3) δ 2.32 (s, 3H), 2.86 (dd, 1H), 3.14-2.94 (m, 3H), 3.32-3.24 (m, 1H), 3.98-3.87 (m, 2H), 4.02 (dd, 1H), 4.11 (bd, 1H), 4.96 (bs, 1H), 6.32-6.30 (m, 1H), 6.61 (dd, 1H), 7.00-6.86 (m, 5H), 7.04 (dd, 1H), 7.34-7.25 (m, 2H); MS (APCI) m/z (rel intensity) 405.4 (100).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07384934B2
Source dataset	uspto-grants-2008_06
ORD ID	ord-c3e61a438dd64f38be2a42411b42e70a
Source note	uspto-grants-2008_06