N,N,N',N'-Tetramethylethylenediamine → HCID 86693028, compound

HRID 2173395Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[N:11][N:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15].[CH3:29][N:30](CCN(C)C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:29]([C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[N:11][N:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15])#[N:30]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of tert-butyl 4-{[2-bromo-4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazine-1-carboxylate (380 mg, 0.84 mmol), Zn(CN)2 (59 mg, 0.51 mmol), Pd2(dba)3 (7 mg, 0.0042 mmol), TMEDA (20 mg, 0.17 mmol), and xantphos (5 mg, 0.0084 mmol) in 3 mL of DMF was stirred under microwave irradiation for 3 min at 160° C. The solvent was removed in vacuum to afford the crude compound, which was purified via prep-TLC to afford tert-butyl 4-{[2-cyano-4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazine-1-carboxylate. 1H-NMR (400 MHz, MeOD) δ ppm 9.82 (s, 1H), 8.31 (d, J=1.6 Hz, 1H), 8.12˜8.16 (m, 1H), 7.68 (d, J=7.8 Hz, 1H), 4.14 (s, 2H), 3.43˜3.72 (m, 8H), 1.48 (s, 9H).

Workup

customThe solvent was removed in vacuum
customto afford the crude compound, which
customwas purified via prep-TLC

Sources & evidence

ORD record: ord-f1e8cf3662804130afafcba343e17d85
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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