Indole → HCID 56985619, compound

HRID 1459714Notes

Reaction equation

HRID 1459714 reaction equation
C(OC(NCC1(O)CCNC1)=O)(C)(C)C.Cl[CH2:17][CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([N:28]3[CH:32]=[N:31][N:30]=[CH:29]3)[CH:26]=2)[NH:21][CH:20]=1.[CH2:33]([NH:40][CH2:41][C:42]1([OH:65])[CH2:47][CH2:46][N:45]([CH2:48]CCC2C3C(=CC=C(N4C=NN=C4)C=3)NC=2)CC1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N1C2C(=CC=CC=2)C=C1>O.CS(C)=O>[CH2:33]([NH:40][CH2:41][C:42]1([OH:65])[CH2:47][CH2:46][N:45]([CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([N:28]4[CH:32]=[N:31][N:30]=[CH:29]4)[CH:26]=3)[NH:21][CH:20]=2)[CH2:48]1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 798Indole2×HCID 11647963HCID 11647963, compoundHCID 537161023-(Boc-aMinoMethyl)-3-hydroxypyrrolidineHCID 54404777HCID 54404777, compound

Product 1

HCID 56985619HCID 56985619, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The title compound was prepared from 3-(t-butyloxycarbonylamino) methyl-3-hydroxypyrrolidine and 1-chloro-2-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]ethane (prepared from 2-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]ethanol), followed by deprotection and functionalisation as described for 4-(benzylamino)methyl-4-hydroxy-1-(3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl)piperidine. mp>56° C. MS, ES+, m/z=417 for (M+H)+ ; δ (360 MHz, D6 -DMSO) 1.60-1.68 (1H, m, CH), 1.80-1.88 (1H, m, CH), 2.40-2.76 (8H, m, 4×CH2N), 2.84 (2H, t, J=7 Hz, CH2 -indole), 3.72 (2H, s, NHCH2Ar), 4.56 (1H, s, OH), 7.17-7.36 (7H, m, Ar--H), 7.47 (1H, d, J=8 Hz, Ar--H), 7.78 (1H, d, J=2 Hz, Ar--H), 9.01 (2H, s, triazole-H), 11.07 (1H, s, indole-NH). (Found: C, 67.40; H, 6.68; N, 19.54. C24H28N6O.0.5 H2O requires C, 67.74; H, 6.87; N, 19.75%).

Sources & evidence

ORD record
ord-32b2292a406b4b119724cf952287e537
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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