2-Nitrophenyl isocyanate → 5-[[2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazoly]carbonylamino]-N-(2-nitrophenyl)-1H-indole-1-carboxamide

HRID 1020370Notes

Reaction equation

HRID 1020370 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[NH:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([NH:21][C:22]([C:24]3[O:28][C:27]([N:29]4[CH2:34][CH2:33][CH2:32][CH:31]([CH3:35])[CH2:30]4)=[N:26][C:25]=3[C:36]([F:39])([F:38])[F:37])=[O:23])=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)=[O:11].N1C2C(=CC(NC(C3OC(N4CCCC(C)C4)=NC=3C(F)(F)F)=O)=CC=2)C=C1.[N+:68](C1C=CC=CC=1N=C=O)([O-:70])=[O:69]>>[CH3:35][CH:31]1[CH2:32][CH2:33][CH2:34][N:29]([C:27]2[O:28][C:24]([C:22]([NH:21][C:17]3[CH:16]=[C:15]4[C:20](=[CH:19][CH:18]=3)[N:12]([C:10]([NH:9][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N+:68]([O-:70])=[O:69])=[O:11])[CH:13]=[CH:14]4)=[O:23])=[C:25]([C:36]([F:39])([F:38])[F:37])[N:26]=2)[CH2:30]1

Participants

4

Reactant 3

HCID 768342-Nitrophenyl isocyanateHCID 67391139N-(2,6-dichlorophenyl)-5-[[2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolyl]carbonylamino]-1H-indole-1-carboxamideHCID 67391262N-(1H-indol-5-yl)-2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

Product 1

HCID 574854435-[[2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazoly]carbonylamino]-N-(2-nitrophenyl)-1H-indole-1-carboxamide

Procedure

Compound 47 was prepared by the general procedure for compound 45, using compound 44 and 2-nitrophenyl isocyanate as starting materials. 1H NMR (500 MHz, DMSO-d6) δ 10.55 (br s, 1H), 10.18 (br s, 1H), 8.14 (br d, 1H, J=8.5 Hz), 8.08 (br s, 1H), 8.05 (br d, 1H, J=8.5 Hz), 8.00 (br d, 1H, J=8.0 Hz), 7.79 (tm, 1H, J=7.6 Hz), 7.72 (br d, 1H, J=8.2 Hz), 7.51 (br d, 1H, J=8.2 Hz), 7.46 (m, 1H), 6.84 (m, 1H), 4.13 (m, 2H), 3.06 (br t, 1H, J=12.0 Hz), 2.76 (br t, 1H, J=11.7 Hz), 1.74 (m, 3H), 1.54 (m, 1H), 1.16 (m, 1H), 0.94 (d, 3H, J=6.3 Hz). MS (M+1): 557.

Sources & evidence

ORD record
ord-6bcf524b9ea3403494d56c882d3f4397
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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