N-Methylbutylamine → HCID 59489629, compound

HRID 1808040Notes

Reaction equation

HRID 1808040 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:24]=[CH:23][C:22]3[CH2:21][CH:20]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Br:31])[CH:26]=4)[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.[CH3:36][NH:37][CH2:38][CH2:39][CH2:40][CH3:41]>C(N(CC)CC)C>[Br:31][C:27]1[CH:26]=[C:25]([CH:20]2[C:19]3[CH:32]=[CH:33][CH:34]=[CH:35][C:18]=3[C:17]3[N:16]=[C:15]([NH:14][C:11]4[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][N:37]([CH2:38][CH2:39][CH2:40][CH3:41])[CH3:36])=[CH:13][CH:12]=4)[N:24]=[CH:23][C:22]=3[CH2:21]2)[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 59489609HCID 59489609, compound

Product 1

HCID 59489629HCID 59489629, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This was synthesized by using 4-(6-(3-bromophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate and N-methylbutylamine and triethylamine as described in general procedure 2 to afford the desired product in 44% yield as a yellow solid. M.p.=66-68° C. 1H 400 MHz NMR (DMSO-d6) δ 9.60 (d, J=3.5 Hz, 1H), 9.36 (bs, 1H), 8.38-8.28 (m, 2H), 7.82 (d, J=8.6 Hz, 2H), 7.57-7.43 (m, 3H), 7.42-7.32 (m, 1H), 7.31-7.20 (m, 3H), 7.15-7.04 (m, 2H), 4.48-4.37 (m, 1H), 3.41-2.88 (m, 8H), 2.84 (d, J=4.7 Hz, 3H), 1.73-1.56 (m, 2H), 1.40-1.26 (m, 2H), 0.93 (t, J=7.4 Hz, 3H). LCMS m/e 541 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-7ebbb9e7b56c41df94a60207d173ce82
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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