HCID 59352086, compound → HCID 59352379, compound

HRID 1407904Notes

Reaction equation

[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]3[C:13]4([C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]([CH2:22][C:23]5[O:24][CH:25]=[C:26]([C:28]([O:30]C)=[O:29])[N:27]=5)[C:14]4=[O:32])[CH2:12][O:11][C:9]3=[CH:10][C:5]=2[O:4][N:3]=1.O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1OC(C(OC)=O)=CC=1>>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]3[C:13]4([C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]([CH2:22][C:23]5[O:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=5)[C:14]4=[O:32])[CH2:12][O:11][C:9]3=[CH:10][C:5]=2[O:4][N:3]=1

Participants

Reactant 2

HCID 59352086HCID 59352086, compound

HCID 59352535HCID 59352535, compound

Product 1

HCID 59352379HCID 59352379, compound

Procedure

Following the procedure as described in EXAMPLE 13 and making non-critical variations using methyl 2-[(3-methyl-2′-oxospiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-1′(2′H)-yl)methyl]-1,3-oxazole-4-carboxylate to replace methyl 5-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]furan-2-carboxylate, 2-[(3-methyl-2′-oxospiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-1′(2′H)-yl)methyl]-1,3-oxazole-4-carboxylic acid was obtained (69%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 13.13 (s, 1H), 8.70 (s, 1H), 7.74-7.71 (m, 1H), 7.40-7.34 (m, 1H), 7.26-7.23 (m, 2H), 7.07-7.02 (m, 2H), 5.28-5.22 (m, 2H), 5.00-4.90 (m, 2H), 2.39 (s, 3H); MS (ES+) m/z 417.8 (M+1).

Sources & evidence

ORD record: ord-3448aab4e8304ef29435b80e13c296c6
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916580B2

Reaction notes

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