Ammonia → HCID 178501031, compound

HRID 1670673Notes

Reaction equation

HRID 1670673 reaction equation
ClC(OCC)=O.[CH3:7][O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:28]=[C:27]([C:29](O)=[O:30])[CH:26]=[N:25][C:24]=3[CH3:32])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10].C[N:34]1CCOCC1.N>C(Cl)Cl.CO>[NH2:34][C:29]([C:27]1[N:28]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([C@H:14]3[CH2:13][CH2:12][C@H:11]([C:9]([O:8][CH3:7])=[O:10])[CH2:16][CH2:15]3)=[CH:18][CH:19]=2)[C:24]([CH3:32])=[N:25][CH:26]=1)=[O:30]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 178501032HCID 178501032, compound2×

Product 1

HCID 178501031HCID 178501031, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (245 μl, 2.54 mmol) was added dropwise to a stirred solution of 6-{4-[trans-4-(methoxycarbonyl)cyclohexyl]phenyl}-5-methylpyrazine-2-carboxylic acid (Intermediate 65-1, 751 mg, 2.12 mmol) and N-methylmorpholine (350 μl, 3.18 mmol) in DCM (20 mL) at 0° C. Ammonia (5 mL of a 7M solution in MeOH) was added. The reaction mixture was allowed to warm up over 1 h then was concentrated and the residue was purified by chromatography eluting with 0-10% MeOH/DCM to give the title compound (226 mg, 30%) as a solid; 1H NMR δ 9.00 (1H, s), 8.08 (1H, s), 7.74 (1H, s), 7.70 (2H, d), 7.40 (2H, d), 3.63 (3H, s), 2.70-2.55 (1H, m), 2.67 (3H, s), 2.50-2.35 (1H, m), 2.10-1.98 (2H, m), 1.96-1.83 (2H, m), 1.65-1.43 (4H, m); MS 354.

Workup

  1. temperatureto warm up over 1 h
  2. concentrationthen was concentrated
  3. customthe residue was purified by chromatography
  4. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-f2e441d12bd343b08ff6209ae78633d2
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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