Carbon Dioxide → HCID 14978602, compound

HRID 2256011Notes

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:19]=[N:20][CH:21]=[CH:22][CH:23]=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:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:5])(=[O:25])[CH3:6]

Participants

Reactant 4

HCID 280Carbon Dioxide

HCID 79724-Methylmorpholine

HCID 310183-Pyridinemethanamine

HCID 62365Isobutyl chloroformate

Product 1

HCID 14978602HCID 14978602, compoundYield 75%

Procedure

Using racemic 19 (3.00 g, 16.39 mmol), 4-methylmorpholine (1.66 g, 16.39 mmol), isobutylchloroformate (2.24 g, 16.39 mmol), and 3-aminomethylpyridine (1.77 g, 16.39 mmol) in the mixed carbonic anhydride protocol gave 3.35 g (75%) of 7: mp 172°-174° C. (recrystallized from EtOAc); Rf 0.27 (8% MeOH/CHCl3); IR (KBr) 3400, 3300, 1640, 1540, 1420, 1360, 820, 740 cm-1 ; 1H NMR (DMSO-d6) δ 1.89 (s, C(O)CH3), 4.32 (d, J=5.8 Hz, CH2), 5.55 (d, J=7.9 Hz, CH), 6.28-6.29 (m, C3H), 6.41-6.43 (m, C4H), 7.32 (dd, J=4.8, 7.7 Hz, C5 'H), 7.58-7.62 (m, C4 'H, C5H), 8.44 (br s, C2 'H, C6 'H), 8.62 (d, J=7.9 Hz, NH), 8.81 (t, J=5.8 Hz, NH); 13C NMR (DMSO-d6) 22.31 (C(O)CH3), 39.98 (CH2), 50.94 (CH), 107.67 (C4), 110.54 (C3), 123.38 (C5 '), 134.57 (C3 '), 134.83 (C4 '), 142.64 (C5), 148.06 (C6 '), 148.55 (C2 '), 150.94 (C2), 168.19 (C(O)NH), 169.26 (C(O)CH3) ppm; mass spectrum (FD) 274 (M+ +1). Anal. (C14H15N3O3) C, H, N. ##STR41##

Sources & evidence

ORD record: ord-b736a15864054e2a8ab612f5d4ef5263
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654301

Reaction notes

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