Ammonium Chloride → HCID 86689681, compound

HRID 1623012Notes

Reaction equation

[C:1]([C:5]1[CH:36]=[CH:35][C:8]([C:9]([NH:11][C@@H:12]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][N:28]=3)=[CH:23][CH:22]=2)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].[N-:39]=[N+:40]=[N-:41].[Na+]>CN(C=O)C.CC(=O)OCC>[N:34]1[NH:39][N:40]=[N:41][C:33]=1[C:30]1[CH:29]=[N:28][C:27]([C:24]2[CH:23]=[CH:22][C:21]([CH2:20][C@H:12]([NH:11][C:9](=[O:10])[C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:36][CH:35]=3)[C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])=[CH:26][CH:25]=2)=[N:32][CH:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a solution of tert-butyl (S)-2-(4-(tert-butyl)benzamido)-3-(4-(5-cyanopyrimidin-2-yl)phenyl)propanoate INT-18 (34 mg, 0.07 mmol) in DMF (2 mL) were added NH4Cl (7.5 mg, 1.4 mmol) and NaN3 (7 mg, 0.1 mmol). The reaction mixture was heated at 100° C. for 3 h then diluted with EA and washed with NaHCO3. The organic layer was dried over Na2SO4, concentrated, and purified by preparatory HPLC to provide 4.6 mg (12%) of tert-butyl (S)-3-(4-(5-(2H-tetrazol-5-yl)pyrimidin-2-yl)phenyl)-2-(4-(tert-butyl)benzamido)propanoate. LCMS-ESI (m/z) calculated for C29H33N7O3: 527.6; no m/z observed, tR=3.83 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 9.35 (s, 2H), 8.42 (d, J=8.1 Hz, 2H), 7.75 (d, J=8.4 Hz, 2H), 7.47 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.2 Hz, 2H), 7.11 (d, J=7.8 Hz, 1H), 5.13 (dd, J=14.4, 7.1 Hz, 1H), 3.28 (ddd, J=21.0, 13.6, 6.7 Hz, 2H), 1.47 (d, J=6.8 Hz, 9H), 1.33 (s, 9H).

Workup

washwashed with NaHCO3
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
custompurified by preparatory HPLC

Sources & evidence

ORD record: ord-302531cd769847caa297c1ec0256c3f7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778923B2

Reaction notes

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