HCID 59352422, compound → HCID 59352238, compound

HRID 1965765Notes

Reaction equation

[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C:23]1[O:24][CH:25]=[C:26]([C:28](O)=[O:29])[N:27]=1.O=[C:32]1C2(COC3C=C4C(=CC2=3)CCO4)C2[C:34](=CC=CC=2)[N:33]1CC1OC(C(O)=O)=CC=1>>[CH3:32][N:33]([CH3:34])[C:28]([C:26]1[N:27]=[C:23]([CH2:22][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]3([CH2:14][O:13][C:12]4[CH:15]=[C:16]5[C:20](=[CH:21][C:11]3=4)[CH2:19][CH2:18][O:17]5)[C:2]2=[O:1])[O:24][CH:25]=1)=[O:29]

Participants

Reactant 2

HCID 59352422HCID 59352422, compound

HCID 68599012HCID 68599012, compound

Product 1

HCID 59352238HCID 59352238, compound

Procedure

Following the procedure as described in EXAMPLE 13.1 and making non-critical variations using 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, N,N-dimethyl-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 (3.0%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.09 (s, 1H), 7.27-6.86 (m, 4H), 6.50 (s, 1H), 6.40 (s, 1H), 5.08 (ABq, 2H), 4.82 (ABq, 2H), 4.52 (t, J=8.6 Hz, 2H), 3.29 (s, 3H), 3.06 (s, 3H), 2.97 (t, J=8.6 Hz, 2H); MS (ES+) m/z 431.8 (M+1).

Sources & evidence

ORD record: ord-32743bc67fa04f36afba4b61d86bb224
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415370B2

Reaction notes

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