Piperidine → HCID 67541427, compound

HRID 1808077Notes

Reaction equation

HRID 1808077 reaction equation
CS(OCCC1C=CC([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)=CC=1)(=O)=O.[NH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]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:22]4[CH:21]=[CH:20][CH:19]=[C:18]([CH2:36][CH2:35][N:37]5[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]5)[CH:17]=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 8082PiperidineHCID 86645590HCID 86645590, compound

Product 1

HCID 67541427HCID 67541427, 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, piperidine and triethylamine as described in general procedure 6 to afford the desired product as hydrochloride salt. M.p.=165-169° C. 1H NMR (DMSO) 400 MHz δ 10.32 (bs, 1H), 9.66 (s, 1H), 8.35-8.30 (m, 2H), 7.77 (s, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.57-7.46 (m, 3H), 7.44-7.42 (m, 1H), 7.28 (t, J=8.0 Hz, 1H), 7.11 (d, J=7.6 Hz, 1H), 7.04-7.00 (m, 1H), 6.86 (d, J=7.2 Hz, 1H), 4.46 (t, J=6.0 Hz, 1H), 3.53-3.48 (m, 2H), 3.28-3.13 (m, 4H), 3.09-3.01 (m, 2H), 2.94-2.84 (m, 2H), 1.81-1.65 (m, 5H), 1.42-1.32 (m, 1H). LCMS m/e 529 [M+H]. Calc. for C31H30Cl2N4.2.08 Hydrochloric acid.0.04 Water.0.33 Ethyl Acetate: C, 61.12; H, 5.52; N, 8.82. Found C, 61.12; H, 5.52; N, 8.82.

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-3c4b4d4ffd8c4a70bc9edcd7b89eac7e
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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