Diisopropylethylamine → HCID 58997228, compound

HRID 251163Notes

Reaction equation

HRID 251163 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:32])[C:5]([CH2:8][N:9]([CH2:16][C:17]2[C:22]([C:23]([CH3:31])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:6][CH:7]=1.[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[NH:38][C:39](N1C=CN=C1)=[O:40].CCN(C(C)C)C(C)C>CN(C=O)C>[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[NH:38][C:39]([N:13]1[CH2:12][CH2:11][CH:10]([N:9]([CH2:8][C:5]2[C:4]([CH3:32])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:16][C:17]2[C:22]([C:23]([CH3:24])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:31])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:15][CH2:14]1)=[O:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 45120888N-(1H-Imidazol-2-yl)-1H-imidazole-1-carboxamideHCID 67272588HCID 67272588, compound

Product 1

HCID 58997228HCID 58997228, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

The amine from above (230 mg, 0.50 mmol), and imidazole-1-carboxylic acid (1H-imidazol-2-yl)-amide (300 mg, 1.0 mmol) were combined in DMF (2.5 mL) and treated with DIPEA (0.52 mL, 3.0 mmol). The solution was stirred at 75° C. for 3 hours and then concentrated under reduced pressure. This afforded, after column chromatography with silica gel (50:1:0.2 CH2Cl2:MeOH:NH4OH), COMPOUND 309 (180 mg, 65%). 1H NMR (CDCl3): δ 1.17 (q, 2H, J=12.3 Hz), 1.55 (d, 2H, J=12.3 Hz), 1.61 (s, 6H), 2.29 (s, 3H), 2.53 (m, 3H), 3.36 (s, 2H), 3.64 (s, 2H), 4.08 (d, 2H, J=12.9 Hz), 6.68 (s, 2H), 7.00 (d, 2H, J=7.5 Hz), 7.08 (m, 1H), 7.19 (m, 3H), 7.36 (s, 1H), 7.85 (d, 1H, J=7.5 Hz), 8.20 (s, 1H), 8.48 (br d, 1H, J=3.3 Hz). 13C NMR (CDCl3) δ 18.87, 28.30 (2C), 31.29 (2C), 42.88, 44.58 (2C), 54.13, 55.33, 58.30, 121.67, 126.02 (2C), 126.32, 128.88 (2C), 130.40, 134.13, 135.41, 137.73, 143.49, 144.91 (2C), 145.48, 146.91 (2C), 149.84, 155.60, 156.53, 158.59. ES-MS m/z 559 (M+H). Anal. Calcd. for C31H36N7OCl.0.3CH2Cl2: C, 64.42; H, 6.32; N, 16.80; Cl, 9.72. Found: C, 64.26; H, 6.35; N, 16.64; Cl, 9.47.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0473c27da68644d39ca1a7f02f9a5511
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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