Triphosgene → 3-Isobutyl-N-(2-(4-methylpiperazin-1-yl)benzyl)-1-oxo-3-phenyl-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide

HRID 1747751Notes

Reaction equation

HRID 1747751 reaction equation
CN1CCN(C2C=CC=CC=2CN)CC1.[CH:16]1([C:22]2([CH2:49][CH:50]([CH3:52])[CH3:51])[C:26]3[CH2:27][N:28]([C:31]([NH:33][CH2:34][CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]4[N:41]4[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]4)=[O:32])[CH2:29][CH2:30][C:25]=3[C:24](=[O:48])[O:23]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(N(CC)CC)C>[CH2:49]([C:22]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:26]2[CH2:27][N:28]([C:31]([NH:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[N:41]3[CH2:42][CH2:43][N:44]([CH3:47])[CH2:45][CH2:46]3)=[O:32])[CH2:29][CH2:30][C:25]=2[C:24](=[O:48])[O:23]1)[CH:50]([CH3:52])[CH3:51]

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 27955682-(4-Methyl-1-piperazinyl)benzenemethanamineHCID 896158213-cyclohexyl-3-isobutyl-N-((2-(4-methylpiperazin-1-yl)cyclohexyl)methyl)-1-oxo-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide

Product 1

HCID 896158183-Isobutyl-N-(2-(4-methylpiperazin-1-yl)benzyl)-1-oxo-3-phenyl-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

An analogous procedure to that described for R06039-275 was used to convert [2-(4-methylpiperazin-1-yl)phenyl]methanamine to 3-cyclohexyl-3-isobutyl-N-((2-(4-methylpiperazin-1-yl)cyclohexyl)methyl)-1-oxo-3,4,6,7-tetrahydrofuro[3,4-c]pyridine-5(1H)-carboxamide using triphosgene and triethylamine. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.82-0.90 (m, 3H), 0.90-1.00 (m, 3H), 1.58-1.73 (m, 1H), 1.74-1.88 (m, 1H), 2.25-2.46 (m, 3H), 2.34 (s, 3H), 2.49-2.67 (m, 4H), 2.98 (t, J=4.90 Hz, 4H), 3.23-3.38 (m, 1H), 3.55 (dt, J=13.56, 5.09 Hz, 1H), 3.93 (dt, J=19.21, 2.64 Hz, 1H), 4.43-4.59 (m, 3H), 6.05 (t, J=5.27 Hz, 1H), 7.02-7.19 (m, 2H), 7.22-7.43 (m, 7H).

Sources & evidence

ORD record
ord-11fee19ab2a948549727d29a4ce0fe21
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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