Triethylamine → N-[(6S,9R)-6-(2,3-Difluorophenyl)-3-ethyl-2,5,6,7,8,9-hexahydro-3H-imidazo[1,2-a]azepin-9-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

HRID 14400

Reaction equation

HRID 14400 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[CH:23]([CH2:26][CH3:27])[CH2:24][N:25]=[C:20]2[C@H:19]([NH2:28])[CH2:18][CH2:17]1.[O:29]=[C:30]1[NH:38][C:33]2=[N:34][CH:35]=[CH:36][CH:37]=[C:32]2[N:31]1[CH:39]1[CH2:44][CH2:43][N:42]([C:45](Cl)=[O:46])[CH2:41][CH2:40]1.C(=O)(O)[O-].[Na+]>ClCCl>[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[CH:23]([CH2:26][CH3:27])[CH2:24][N:25]=[C:20]2[C@H:19]([NH:28][C:45]([N:42]2[CH2:41][CH2:40][CH:39]([N:31]3[C:32]4[C:33](=[N:34][CH:35]=[CH:36][CH:37]=4)[NH:38][C:30]3=[O:29])[CH2:44][CH2:43]2)=[O:46])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 222932214-(2-Oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chlorideHCID 67174547(6S,9R)-6-(2,3-Difluorophenyl)-3-ethyl-2,5,6,7,8,9-hexahydro-3H-imidazo[1,2-a]azepin-9-amine

Product 1

HCID 11606278N-[(6S,9R)-6-(2,3-Difluorophenyl)-3-ethyl-2,5,6,7,8,9-hexahydro-3H-imidazo[1,2-a]azepin-9-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamideYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (17 μL, 0.124 mmol) was added to a solution of the (6S,9R)-6-(2,3-difluorophenyl)-3-ethyl-2,5,6,7,8,9-hexahydro-3H-imidazo[1,2-a]azepin-9-amine (13 mg, 0.035 mmol) and 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carbonyl chloride (15 mg, 0.053 mmol) in dichloromethane (1 mL). After 18 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by reverse phase HPLC(C-18, 95% water/acetonitrile 30% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (8 mg). MS 538.2710 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by reverse phase HPLC(C-18, 95% water/acetonitrile 30% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-3f272dfef6e9454b9e4770df6c802e7a
Source dataset
uspto-grants-2010_06
Patent number
US07732438B2

Linked notes

Loading…