1-Adamantanecarbonyl chloride → Adamantane-1-carboxylic acid [2-(4-adamantanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

HRID 854087Notes

Reaction equation

HRID 854087 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:29][C:11]3[CH:12]=[N:13][C:14]([NH:16][C:17]([C:19]45[CH2:28][CH:23]6[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]6)[CH2:20]4)[CH2:26]5)=[O:18])=[CH:15][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[C:30]12([C:40](Cl)=[O:41])[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2>C1COCC1.N1C=CC=CC=1>[C:30]12([C:40]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[NH:29][C:11]5[CH:12]=[N:13][C:14]([NH:16][C:17]([C:19]67[CH2:26][CH:25]8[CH2:24][CH:23]([CH2:22][CH:21]([CH2:27]8)[CH2:20]6)[CH2:28]7)=[O:18])=[CH:15][C:10]=5[N:9]=4)=[CH:4][CH:3]=3)=[O:41])[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2

Participants

4

Reactant 2

HCID 989151-Adamantanecarbonyl chlorideHCID 58932924Adamantane carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

Product 1

HCID 86592843Adamantane-1-carboxylic acid [2-(4-adamantanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amideYield 56.1%

Reagents, catalysts & solvents 1

HCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of amine 14 (0.200 g, 0.50 mmol) in dry THF-Pyridine (10 ml/0.400 ml), adamantane carbonyl chloride (0.150 g, 0.75 mmol) was added and stirred at room temperature under argon overnight. The reaction was quenched with water and stirred at room temperature for 30 min. The yellow solid was filtered and passed through SiO2 gel using CH2Cl2: MeOH (95:5) as a eluent that yielded the desired product 15 (0.150 g, 50%). M.p. 265° C.; 1HNMR (DMSO-d6, 500 MHz): δ 13.02 (1H, brs, NH), 9.48 (1H, brs, NH), 9.37 (1H, brs, NH), 8.64 (1H, s), 8.24 (1H, s), 8.08 (2H, d, J=5.0 Hz), 7.88 (2H, d, J=5.0 Hz), 2.03-1.60 (30H, m). EIMS m/z: 449.6 (M+1); Anal (C34H39N5O2×0.85 H2O) C, H, N.

Workup

  1. customThe reaction was quenched with water
  2. stirringstirred at room temperature for 30 min
  3. filtrationThe yellow solid was filtered

Sources & evidence

ORD record
ord-5c74ead957a5484b845846b1c6228aa8
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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