Hydrochloric Acid → HCID 178457849, compound

HRID 518695Notes

Reaction equation

HRID 518695 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=1.[O:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][NH2:32])[CH2:26][CH2:25]1.Cl>CC(O)C>[CH:18]([NH:17][C:15]([C@H:12]1[CH2:13][CH2:14][C@@H:9]([NH:8][C:6]2[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=[C:2]([NH:32][CH2:31][CH2:30][N:27]3[CH2:28][CH2:29][O:24][CH2:25][CH2:26]3)[CH:7]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4082852-Morpholinoethylamine2×HCID 178457831HCID 178457831, compound

Product 1

HCID 178457849HCID 178457849, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A glass microwave reaction vessel was charged with cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (200 mg, 0.587 mmol) and 2-morpholinoethanamine (0.092 mL, 0.704 mmol) in 2-propanol. A drop of HCl (2N in ether) was added, and the reaction mixture was stirred and irradiated in a microwave at 175° C. for 2 hours. Additional 2-morpholinoethanamine (0.030 mL, 0.24 mmol) was added, and the mixture was heated an additional 20 minutes. The mixture was evaporated and the residue diluted with 10% IPA/DCM, washed with water, brine, and the organic layer dried over Na2SO4. The mixture was purified via flash chromatography using a linear gradient of 0% to 10% of 1% NH4OH in MeOH in DCM. Intermediate cis-N-isopropyl-4-(2-(2-morpholinoethylamino)-5-nitropyridin-4-ylamino)cyclohexanecarboxamide was isolated as a yellow film (128 mg).

Workup

  1. customA glass microwave reaction vessel
  2. customirradiated in a microwave at 175° C. for 2 hours
  3. temperaturethe mixture was heated an additional 20 minutes
  4. customThe mixture was evaporated
  5. additionthe residue diluted with 10% IPA/DCM
  6. washwashed with water, brine
  7. dry with materialthe organic layer dried over Na2SO4
  8. customThe mixture was purified via flash chromatography

Sources & evidence

ORD record
ord-c3911613c264477d82ae6aba01b3d60c
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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