N-Methylbutylamine → HCID 67427968, compound

HRID 1808070Notes

Reaction equation

HRID 1808070 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][C@@H:20]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][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>[ClH:31].[CH2:38]([N:37]([CH3:36])[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][C@@H:20]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][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)[CH2:39][CH2:40][CH3:41]

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 59489845HCID 59489845, compound

Product 1

HCID 67427968HCID 67427968, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This was synthesized by using (S)-4-(6-(4-chlorophenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate, N-methylbutan-1-amine and triethylamine as described in general procedure 2 to give a yellow solid. M.p.=75-77° C. 1H NMR 400 MHz (DMSO-d6) δ 9.90 (s, br, 1H), 9.59 (s, 1H), 8.30 (m, 2H), 7.79 (d, J=8.4 Hz, 2H), 7.50-7.44 (m, 2H), 7.31 (m, 2H), 7.22 (d, J=8.8 Hz, 2H), 7.10 (m, 4H), 4.42 (t, J=5.6 Hz, 1H), 3.28-2.86 (m, 8H), 2.78 (d, J=5.2 Hz, 3H), 1.67-1.59 (m, 2H), 1.33-1.27 (m, 2H), 0.90 (t, J=7.2 Hz, 3H). LCMS m/e 497 (M+H).

Workup

  1. customThis was synthesized
  2. customto give a yellow solid

Sources & evidence

ORD record
ord-a40925b086654e16abff1c53524c158d
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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