4-[(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)methyl]-3,4-dihydro-2H-chromene-8-carbonitrile → 4-({4-[(1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetyl]piperazin-1-yl}methyl)-3,4-dihydro-2H-chromene-8-carbonitrile

HRID 2173437Notes

Reaction equation

HRID 2173437 reaction equation
N1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH:22]4[C:31]5[C:26](=[C:27]([C:32]#[N:33])[CH:28]=[CH:29][CH:30]=5)[O:25][CH2:24][CH2:23]4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][CH:7]=2)C=NN=N1.C(C1C2C(=C(C#N)C=CC=2)OCC1)=O.O=C(N1CCNCC1)CC1C=CC2[C:55](=[O:58])[O:56][CH2:57]C=2C=1>>[O:58]=[C:55]1[C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH:22]4[C:31]5[C:26](=[C:27]([C:32]#[N:33])[CH:28]=[CH:29][CH:30]=5)[O:25][CH2:24][CH2:23]4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH2:57][O:56]1

Participants

4

Reactant 3

HCID 675157554-[(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)methyl]-3,4-dihydro-2H-chromene-8-carbonitrileHCID 675168485-[2-oxo-2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-oneHCID 772306634-formyl-3,4-dihydro-2H-chromene-8-carbonitrile

Product 1

HCID 675182564-({4-[(1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetyl]piperazin-1-yl}methyl)-3,4-dihydro-2H-chromene-8-carbonitrile

Procedure

4-({4-[(1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetyl]piperazin-1-yl}methyl)-3,4-dihydro-2H-chromene-8-carbonitrile was prepared in an analogous fashion to that described for the synthesis of 4-[(4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)methyl]-3,4-dihydro-2H-chromene-8-carbonitrile above starting from 4-formyl-3,4-dihydro-2H-chromene-8-carbonitrile and 5-[2-oxo-2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.85 (d, J=7.8 Hz, 1H), 7.31˜7.38 (m, 4H), 6.8 (t, J=7.8 Hz, 1H), 5.24 (s, 2H), 4.15˜4.45 (m, 2H), 3.8 (s, 2H), 3.4˜3.73 (m, 4H), 2.88˜2.95 (m, 1H), 2.3˜2.52 (m, 6H), 1.97˜2.1 (m, 2H).

Sources & evidence

ORD record
ord-2530f6ab3aff427f84f95aaae28e76ae
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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