Piperazine → HCID 59489754, compound

HRID 1808074Notes

Reaction equation

CS(OCC[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:24]=[CH:23][C:22]3[CH2:21][C@@H:20]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])[C:19]4[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=4[C:17]=3[N:16]=2)=[CH:10][CH:9]=1)(=O)=O.[NH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[CH2:42](N(CC)CC)[CH3:43]>>[F:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C@H:20]1[C:19]2[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=2[C:17]2[N:16]=[C:15]([NH:14][C:11]3[CH:12]=[CH:13][CH:8]=[C:9]([CH2:42][CH2:43][N:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)[CH:10]=3)[N:24]=[CH:23][C:22]=2[CH2:21]1

Participants

Reactant 3

HCID 4837Piperazine

HCID 8471Triethylamine

HCID 59489613HCID 59489613, compound

Product 1

HCID 59489754HCID 59489754, compound

Procedure

This was synthesized by using (R)-4-(6-(2-fluorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate, piperazine and triethylamine as described in general procedure 6 to afford the desired product. Yellow solid (46%). M.p.=165-167° C. 1H NMR 400 MHz (DMSO-d6) δ 9.82 (s, 1H), 9.71 (s, 1H), 7.83 (s, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.61 (t, J=7.2 Hz, 1H), 7.48 (t, J=7.6 Hz, 1H), 7.33-7.22 (m, 3H), 7.08-7.02 (m, 2H), 7.91 (d, J=7.6 Hz, 1H), 6.11 (t, J=7.6 Hz, 1H), 4.68 (t, J=6.8 Hz, 1H), 3.79 (br, 2H), 3.56-3.38 (m, 7H), 3.19-3.09 (m, 4H), 2.93 (t, J=16.4 Hz, 2H). LCMS m/e 480 (M+H).

Workup

customThis was synthesized

Sources & evidence

ORD record: ord-bb574d617709437babc711c393b8b386
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357694B2

Reaction notes

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