(S)-2-Trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine → HCID 135474385, compound

HRID 131434Notes

Reaction equation

HRID 131434 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.[CH3:47][O:48][CH2:49][C@H:50]1[CH2:55]N[CH2:53][CH2:52][NH:51]1>>[CH3:47][O:48][CH2:49][C@@H:50]1[NH:51][CH2:52][CH2:53][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)[CH2:55]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 45092759HCID 45092759, compoundHCID 13552565010H-Thieno[2,3-b][1,5]benzodiazepin-4-amine, 2-methyl-, hydrochloride (1:1)

Product 1

HCID 135474385HCID 135474385, compoundYield 41%

Procedure

By using a similar coupling method to (S)-2-trifluoromethyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b, e][1,4]diazepine, using 2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (1.9 g) and (R)-2-methoxymethyl-piperazine (2.6 g) affords the title compound as a yellow solid (974 mg, 41%); mp 87-95° C.: 1H NMR (CDCl3) δ 2.32 (d, 3H), 2.69 (dd, 1H), 3.10-2.87 (m, 4H), 3.33 (dd, 1H), 3.38 (s, 3H), 3.49-3.43 (m, 1H), 3.94 (d, 1H), 4.02 (d, 1H), 4.98 (s, 1H), 6.30 (s, 1H), 6.61 (dd, 1H), 6.88 (dt, 1H), 6.97 (dt, 1H), 7.03 (dd, 1H); MS (APCI) m/z (rel intensity) 343.3 (100).

Sources & evidence

ORD record
ord-31b2aaf09aef4fbb83cc51d5699bce25
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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