Ammonia → HCID 59352533, compound

HRID 1407900Notes

Reaction equation

HRID 1407900 reaction equation
N.Cl.C[NH:4]C.[O:6]=[C:7]1[C:15]2([CH2:19][O:18][C:17]3[CH:20]=[C:21]4[C:25](=[CH:26][C:16]2=3)[CH2:24][CH2:23][O:22]4)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]1[CH2:27][C:28]1[O:29][CH:30]=[C:31]([C:33](O)=[O:34])[N:32]=1.O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1OC(C(O)=O)=CC=1>O1CCOCC1>[O:6]=[C:7]1[C:15]2([CH2:19][O:18][C:17]3[CH:20]=[C:21]4[C:25](=[CH:26][C:16]2=3)[CH2:24][CH2:23][O:22]4)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]1[CH2:27][C:28]1[O:29][CH:30]=[C:31]([C:33]([NH2:4])=[O:34])[N:32]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10473Dimethylamine, hydrochlorideHCID 59352422HCID 59352422, compoundHCID 68599012HCID 68599012, compound

Product 1

HCID 59352533HCID 59352533, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the procedure as described in EXAMPLE 13.1 and making non-critical variations using 4 M ammonia solution in dioxane to replace dimethylamine hydrochloride, 2-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]-1,3-oxazole-4-carboxylic acid to replace 5-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3-indol]-1′(2′H)-yl)methyl]furan-2-carboxylic acid, 2-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]-1,3-oxazole-4-carboxamide was obtained (19%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H), 7.53 (d, J=10.2 Hz, 2H), 7.33-6.99 (m, 4H), 6.54 (s, 1H), 6.38 (s, 1H), 5.22-5.01 (m, 2H), 4.75 (ABq, 2H), 4.46 (t, J=8.8 Hz, 2H), 2.92 (t, J=8.6 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ177.3, 161.9, 161.6, 160.9, 159.2, 143.2, 142.2, 136.8, 132.5, 129.2, 124.1, 123.8, 120.8, 120.4, 119.7, 109.6, 92.8, 80.0, 72.5, 57.3, 37.4, 28.7; MS (ES+) m/z 403.8 (M+1).

Sources & evidence

ORD record
ord-bbbd810a67dd4a398c589901848bc9fb
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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