Ammonia → HCID 59352778, compound

HRID 2385486Notes

Reaction equation

HRID 2385486 reaction equation
N.C1(C[NH2:9])CCCCC1.[O:10]=[C:11]1[C:19]2([CH2:23][O:22][C:21]3[CH:24]=[C:25]4[C:29](=[CH:30][C:20]2=3)[CH2:28][CH2:27][O:26]4)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH2:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=O)=[CH:34][CH:33]=1.O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1C=C(C=CC=1)C(O)=O>ClCCl>[O:10]=[C:11]1[C:19]2([CH2:23][O:22][C:21]3[CH:24]=[C:25]4[C:29](=[CH:30][C:20]2=3)[CH2:28][CH2:27][O:26]4)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]1[CH2:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH2:9])=[O:38])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 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 59352778HCID 59352778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in EXAMPLE 12 and making non-critical variations using ammonia in dry dichloromethane 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, 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 (81%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ7.78 (d, J=7.9 Hz, 2H), 7.34 (d, J=7.9 Hz, 2H), 7.20-7.07 (m, 2H), 6.99 (t, J=7.4 Hz, 1H), 6.85 (s, 1H), 6.71 (d, J=7.6 Hz, 1H), 6.41 (br s, 1H), 6.35 (br s, 1H), 6.20 (s, 1H), 4.94 (ABq, 2H), 4.78 (ABq, 2H), 4.46 (t, J=8.5 Hz, 2H), 2.91 (t, J=8.5 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ177.6, 168.7, 161.5, 160.9, 141.4, 139.3, 132.7, 132.1, 128.4, 127.8, 127.0, 123.6, 123.3, 119.6, 118.4, 108.8, 92.8, 80.2, 72.0, 57.3, 43.4, 28.6; MS (ES+) m/z 413.1 (M+1).

Sources & evidence

ORD record
ord-13a14ac099aa438988c137aba2468c25
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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