Phenyl Bromoacetate → Phenyl 5-[[2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolyl]carbonylamino]-1H-indole-1-acetate

HRID 1020371Notes

Reaction equation

HRID 1020371 reaction equation
ClC1C=CC=C(Cl)C=1N[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.N1C2C(=CC(NC(C3OC(N4CCCC(C)C4)=NC=3C(F)(F)F)=O)=CC=2)C=C1.BrC[C:70]([O:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)=[O:71]>>[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]([CH2:10][C:70]([O:72][C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)=[O:71])[CH:13]=[CH:14]4)=[O:23])=[C:25]([C:36]([F:38])([F:37])[F:39])[N:26]=2)[CH2:30]1

Participants

4

Reactant 3

HCID 564919Phenyl BromoacetateHCID 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 67391617Phenyl 5-[[2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolyl]carbonylamino]-1H-indole-1-acetate

Procedure

Compound 48 was prepared by the general procedure for compound 45, by using compound 44 and phenyl 2-bromoacetate as starting materials. 1H NMR (500 MHz, DMSO-d6) δ 10.22 (br s, 1H), 8.29 (m, 1H), 8.08 (m, 1H), 7.96 (dd, 1H, J=3.5, 13.3 Hz), 7.58 (m, 1H), 7.45 (m, 1H), 7.34 (m, 2H), 7.07 (d, 1H, J=8.5 Hz), 6.99 (t, 1H, J=7.4 Hz), 6.85 (m, 1H), 4.84 (s, 2H), 4.15 (d, 1H, J=13.2 Hz), 4.10 (d, 1H, J=13.6 Hz), 3.06 (t, 1H, J=12.0 Hz), 2.76 (dd, 1H, J=11.0, 12.3 Hz), 1.71 (m, 3H), 1.54 (m, 1H), 1.15 (m, 1H); 0.94 (d, 3H, J=6.3 Hz). MS (M+1): 527.

Sources & evidence

ORD record
ord-97ee98ba7cd5439da29ee14765d8f4ce
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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