N-methyl-2-pyrrolidone → 4'-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid (1-methyl-2-morpholin-4-yl-ethyl)-amide

HRID 77765Notes

Reaction equation

CCN=C=NCCCN(C)C.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([N:25]3[CH:29]=[N:28][N:27]=[N:26]3)[CH:22]=[C:21]([C:30](O)=[O:31])[CH:20]=2)=[CH:15][CH:14]=1.C1C=CC2N(O)N=NC=2C=1.CN1C(=O)CCC1.[CH3:50][C@H:51]([NH2:59])[CH2:52][N:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1>C(Cl)Cl>[CH3:50][CH:51]([NH:59][C:30]([C:21]1[CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=2)[CH:24]=[C:23]([N:25]2[CH:29]=[N:28][N:27]=[N:26]2)[CH:22]=1)=[O:31])[CH2:52][N:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1

Participants

Conditions

Temperature: 0 °C

Procedure

EDCI (54.0 mg, 0.282 mmol) was added in one portion at 0° C. to a solution of 4′-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid (60.0 mg, 0.214 mmol), HOBt (40.0 mg, 0.296 mmol) and NMP (101.5 mg, 1.000 mmol) in CH2Cl2(3 mL). After the reaction stirred at 0° C. for 1 hour, (S)-1-Methyl-2-morpholin-4-yl-ethylamine (50.0 mg, 0.230 mmol) was added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. Solvent was removed under reduced pressure and the residue was purified by column chromatography (EtOAc) to afford 4′-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid (1-methyl-2-morpholin-4-yl-ethyl)-amide as a white solid (70 mg, 81%). MS (M+H)=407.

Workup

temperatureto warm to room temperature
stirringwas stirred overnight
customSolvent was removed under reduced pressure
customthe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record: ord-c13de65dc4334341a39f8ac8cdc6c8a7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841336B2

Reaction notes

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