N-Methylbutylamine → HCID 59490173, compound

HRID 1808054Notes

Reaction equation

HRID 1808054 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]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])[C:19]4[CH:35]=[CH:36][CH:37]=[CH:38][C:18]=4[C:17]=3[N:16]=2)=[CH:10][CH:9]=1)(=O)=O.[CH3:39][NH:40][CH2:41][CH2:42][CH2:43][CH3:44]>C(N(CC)CC)C>[CH2:41]([N:40]([CH3:39])[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]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])[C:19]4[CH:35]=[CH:36][CH:37]=[CH:38][C:18]=4[C:17]=3[N:16]=2)=[CH:10][CH:9]=1)[CH2:42][CH2:43][CH3:44]

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 86645589HCID 86645589, compound

Product 1

HCID 59490173HCID 59490173, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

This was synthesized by using 4-(6-(2-(trifluoromethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-ylamino)phenethyl methanesulfonate, N-methylbutan-1-amine and triethylamine as described in general procedure 2 to afford the desired product. M.p.=80-82° C.; 1H NMR 400 MHz (DMSO-d6) δ 9.54 (s, 1 H); 8.38-8.35 (m, 2 H), 7.82-7.75 (m, 3 H), 7.58 (t, 1 H), 7.51-7.40 (m, 3 H), 7.27 (d, J=8.0 Hz, 1 H), 7.17 (d, J=8.4 Hz, 2 H), 6.76 (d, J=7.6 Hz, 1 H), 4.64 (t, J=8 Hz, 1 H), 3.19-3.12 (m, 2 H), 2.68-2.65 (m, 2 H), 2.55-2.51 (m, 2), 2.37-2.33 (m, 2 H), 2.21 (s, 3 H), 1.40-1.36 (m, 2 H), 1.30-1.23 (m, 2 H), 0.88 (t, J=7.2 Hz, 3 H). LCMS m/e 531 (M+H).

Workup

  1. customThis was synthesized

Sources & evidence

ORD record
ord-105824e0bd5f4bd3a67a774749b6614e
Source dataset
uspto-grants-2013_01
Patent number
US08357694B2

Reaction notes

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