2-Methoxyethylamine → HCID 59352733, compound

HRID 2385495Notes

Reaction equation

HRID 2385495 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-992a89eaa31b4f948af10454ecb0d6df
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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