(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

HRID 131438Notes

Reaction equation

HRID 131438 reaction equation
FC(F)(F)C1C=CC2NC3C=CC=CC=3N=C(N3CCN[C@@H](CCOC)C3)C=2C=1.Cl.[CH3:31][C:32]1[S:41][C:40]2[NH:39][C:38]3[CH:42]=[CH:43][CH:44]=[CH:45][C:37]=3[N:36]=[C:35]([NH2:46])[C:34]=2[CH:33]=1.[O:47]([CH2:54][C@H:55]1[CH2:60]N[CH2:58][CH2:57][NH:56]1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[O:47]([CH2:54][C@@H:55]1[NH:56][CH2:57][CH2:58][N:46]([C:35]2[C:34]3[CH:33]=[C:32]([CH3:31])[S:41][C:40]=3[NH:39][C:38]3[CH:42]=[CH:43][CH:44]=[CH:45][C:37]=3[N:36]=2)[CH2:60]1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

4

Reactant 3

HCID 10250638(S)-2-Trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepineHCID 69214041HCID 69214041, compoundHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 135546110(R)-10-(3-Phenoxymethyl-piperazin-1-yl)-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azuleneYield 39.9%

Procedure

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).

Sources & evidence

ORD record
ord-c3e61a438dd64f38be2a42411b42e70a
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

Loading…