Triethylamine → N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-pyridin-2-ylacetamide

HRID 452254Notes

Reaction equation

HRID 452254 reaction equation
CC1(C)C[CH:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[O:3]1.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([OH:23])=O.CCN=C=NCCCN(C)C.[ClH:35].[CH:36]1[CH:37]=[CH:38][C:39]2N(O)N=N[C:40]=2[CH:41]=1.C(N(CC)CC)C>ClCCl>[Cl:35][C:36]1[CH:41]=[C:40]2[C:39](=[CH:38][CH:37]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:21](=[O:23])[CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 853182-Pyridineacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153387052,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 44132277N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-pyridin-2-ylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from Intermediate 2 (200 mg, 0.898 mmol) and 2-pyridylacetic acid (234 mg, 1.348 mmol) in presence of EDCI.HCl (258 mg, 1.348 mmol), HOBt (206 mg, 1.348 mmol) and triethylamine (375 μl, 2.696 mmol) in dichloromethane (10 ml) as described in Example 1 to give 151 mg of the product as a white solid; IR (KBr) 3272, 2936, 1644, 1477, 1265, 812 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 1.65-1.88 (m, 3H), 2.02-2.20 (m, 3H), 2.25-2.35 (m, 2H), 3.71 (q, J=12.0 Hz, 2H), 5.00-5.15 (m, 1H), 6.73 (t, J=7.8 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 7.10-7.20 (m, 2H), 7.22-7.30 (m, 1H), 7.70-7.80 (m, 1H), 8.49 (s, 1H), 8.62 (d, J=8.4 Hz, 1H); ESI-MS (m/z) 343.21 (M+H)+.

Sources & evidence

ORD record
ord-6cdbf3dfb03d4735b1565795d6602ff2
Source dataset
uspto-grants-2013_07
Patent number
US08487121B2

Reaction notes

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