Carbon Dioxide → HCID 14978603, compound

HRID 2256012Notes

Reaction equation

C[N:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH2:8]([O:12][C:13](Cl)=O)[CH:9]([CH3:11])C.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C(=O)=[O:25]>>[C:7]([NH:2][CH:3]([C:13]1[O:12][CH:8]=[CH:9][CH:11]=1)[C:4]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=[O:5])(=[O:25])[CH3:6]

Participants

Reactant 4

HCID 280Carbon Dioxide

HCID 79724-Methylmorpholine

HCID 62365Isobutyl chloroformate

HCID 773174-Pyridinemethanamine

Product 1

HCID 14978603HCID 14978603, compoundYield 76%

Procedure

Making use of racemic 19 (3.00 g, 16.39 mmol), 4-methylmorpholine (1.66 g, 16.39 mmol), isobutylchloroformate (2.24 g, 16.39 mmol), and 4-aminomethylpyridine (1.77 g, 16.39 mmol) in the mixed carbonic anhydride method, gave 3.40 g (76%) of 8: mp 168°-170° C. (recrystallized from EtOAc); Rf 0.31 (8% MeOH/CHCl3); IR (KBr) 3180, 1650 (br), 1480, 1400, 1340, 780, 740 cm-1 ; 1H NMR (DMSO-d6) δ 1.90 (s, C(O)CH3), 4.32 (d, J=5.7 Hz, CH2), 5.57 (d, J=7.8 Hz, CH), 6.32-6.34 (m, C3H), 6.42-6.43 (m, C4H), 7.19 (d, J=4.9 Hz, C3 'H, C5 'H), 7.64 (s, C5H), 8.46 (d, J=4.9 Hz, C2 'H, C6 'H), 8.64 (d, J=7.8 Hz, NH), 8.84 (t, J=5.7 Hz, NH); 13C NMR (DMSO-d6) 22.27 (C(O)CH3), 41.26 (CH2), 50.99 (CH), 107.74 (C4), 110.54 (C3), 121.87 (C3 ', C5 '), 142.63 (C5), 148.17 (C4 '), 149.35 (C2 ', C6 '), 150.82 (C2), 168.35 (C(O)NH), 169.29 (C(O)CH3) ppm; mass spectrum (FD) 274 (M+ +1). Anal. (C14H15N3O3) C, H, N. ##STR42##

Sources & evidence

ORD record: ord-ce766b4a7edc4f17a0c25172583bccef
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654301

Reaction notes

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