HCID 43252569, compound → HCID 67427141, compound

HRID 1808076Notes

Reaction equation

HRID 1808076 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][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=4)[C:19]4[CH:33]=[CH:34][CH:35]=[CH:36][C:18]=4[C:17]=3[N:16]=2)=[CH:10][CH:9]=1)(=O)=O.[CH3:37][O:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48]N)[CH2:43][CH2:42]1>C(N(CC)CC)C>[ClH:31].[Cl:32][C:27]1[CH:26]=[C:25]([C@H:20]2[C:19]3[CH:33]=[CH:34][CH:35]=[CH:36][C:18]=3[C:17]3[N:16]=[C:15]([NH:14][C:11]4[CH:12]=[CH:13][CH:8]=[C:9]([CH2:48][CH2:47][N:44]5[CH2:45][CH2:46][N:41]([CH2:40][CH2:39][O:38][CH3:37])[CH2:42][CH2:43]5)[CH:10]=4)[N:24]=[CH:23][C:22]=3[CH2:21]2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

4

Reactant 2

HCID 43252569HCID 43252569, compoundHCID 86645590HCID 86645590, compound

Product 1

HCID 67427141HCID 67427141, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This was synthesized by using (S)-4-(6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate, 2-(4-(2-methoxyethyl)piperazin-1-yl)ethanamine and triethylamine as described in general procedure 6 to afford the desired product as hydrochloride salt. M.p.=220-225° C. 1H NMR (DMSO) 400 MHz δ 12.25 (bs, 1H), 11.70 (bs, 1H), 9.67 (s, 1H), 8.34-8.30 (m, 2H), 7.79 (s, 1H), 7.67 (d, J=9.6 Hz, 1H), 7.58 (t, J=7.6 Hz, 1H), 7.52-7.41 (m, 3H), 7.28 (t, J=8.0 Hz, 1H), 7.10 (d, J=7.6 Hz, 1H), 7.03-6.99 (m, 1H), 6.89 (d, J=8.0 Hz, 1H), 4.46 (t, J=6.4 Hz, 1H), 3.90-3.68 (m, 6H), 3.68-3.32 (m, 8H), 3.28 (s, 3H), 3.18-3.12 (m, 2H), 3.11-3.05 (m, 2H). LCMS: 588 m/e [M+H]. Calc. for C33H35Cl2N5.2.60 Hydrochloric acid.1.42 Water.0.03 Ethyl Acetate: C, 55.90; H, 5.76; N, 9.84. Found C, 55.91; H, 5.76; N, 9.84.

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-c014cc14bc4d4eda8ef0f4154181734d
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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