2-Methoxyethylamine → HCID 59352733, compound

HRID 1965748Notes

Reaction equation

HRID 1965748 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C1(CN)CCCCC1.[O:14]=[C:15]1[C:23]2([CH2:27][O:26][C:25]3[CH:28]=[C:29]4[C:33](=[CH:34][C:24]2=3)[CH2:32][CH2:31][O:30]4)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]1[CH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1.O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1C=C(C=CC=1)C(O)=O>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:40](=[O:41])[C:39]1[CH:43]=[CH:44][C:36]([CH2:35][N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3([CH2:27][O:26][C:25]4[CH:28]=[C:29]5[C:33](=[CH:34][C:24]3=4)[CH2:32][CH2:31][O:30]5)[C:15]2=[O:14])=[CH:37][CH:38]=1

Participants

5

Reactant 4

HCID 80182-MethoxyethylamineHCID 76688CyclohexanemethylamineHCID 593522533-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]benzoic acidHCID 593526094-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]benzoic acid

Product 1

HCID 59352733HCID 59352733, compound

Procedure

Following the procedure as described in EXAMPLE 12 and making non-critical variations using 2-methoxyethylamine to replace cyclohexanemethylamine, and 4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3-indol]-1′(2′H)-yl)methyl]benzoic acid to replace 3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzoic acid, N-(2-methoxyethyl)-4-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3-indol]-1′(2′H)-yl)methyl]benzamide was obtained (49%) as a colorless solid: mp 182-183° C.; 1H NMR (300 MHz, CDCl3) δ7.81-7.73 (m, 2H), 7.44-7.37 (m, 2H), 7.23-7.15 (m, 2H), 7.07-7.00 (m, 1H), 6.77-6.70 (m, 1H), 6.56-6.41 (m, 3H), 5.00 (ABq, 2H), 4.85 (ABq, 2H), 4.60-4.51 (m, 2H), 3.68-3.60 (m, 2H), 3.59-3.52 (m, 2H), 3.38 (s, 3H), 3.08-2.94 (m, 2H); 13C NMR (75 MHz, CDCl3) δ177.9, 166.9, 161.9, 161.3, 141.8, 139.3, 134.1, 132.6, 128.7, 127.6, 127.5, 124.0, 123.6, 120.0 (2C), 118.8, 109.1, 93.3, 80.6, 72.4, 71.1, 58.8, 57.7, 43.8, 39.7, 29.0; MS (ES+) m/z 471.1 (M+1).

Sources & evidence

ORD record
ord-520eced22bec4bc98a9e11d9a55a296a
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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