Ammonia → HCID 178513914, compound

HRID 1713761Notes

Reaction equation

HRID 1713761 reaction equation
ClC(OCC)=O.[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[O:19][C:18]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C@H:29]3[CH2:34][CH2:33][C@H:32]([CH2:35][C:36]([OH:38])=O)[CH2:31][CH2:30]3)=[CH:25][CH:24]=2)=[O:21])=[N:17][N:16]=1.C[N:40]1CCOCC1.N>C(Cl)Cl.CO>[NH2:40][C:36](=[O:38])[CH2:35][C@H:32]1[CH2:33][CH2:34][C@H:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:20]([C:18]3[O:19][C:15]([NH:14][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[F:7])=[N:16][N:17]=3)=[O:21])=[CH:28][CH:27]=2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 178525547HCID 178525547, compound

Product 1

HCID 178513914HCID 178513914, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (0.056 mL, 0.58 mmol) was added dropwise to a stirred solution of (trans-4-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-phenyl}cyclohexyl)acetic acid (Example 118) (170 mg, 0.39 mmol) and N-methyl morpholine (0.064 mL, 0.58 mmol) in DCM (5 mL) at 0° C. The mixture was stirred for 40 minutes then ammonia (2 mL of a 7M solution in MeOH) was added and stirring was continued for 16 h whilst warming to ambient temperature. Volatile material was removed by evaporation and the residue was triturated with water and washed with 10% ammonium hydroxide solution (10 mL) followed by ether (10 mL) and dried under reduced pressure to give the title compound (121 mg, 71%) as a solid; 1H NMR δ 0.98-1.15 (m, 2H), 1.33-1.50 (m, 2H), 1.63-1.85 (m, 5H), 1.95 (d, 2H), 2.37-2.44 (m, 1H), 6.75 (s, 1H), 7.10-7.35 (m, 5H), 7.66 (d, 2H), 8.03 (t, 1H), 10.78 (s, 1H), 10.99 (s, 1H); MS m/e MH+ 438.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h
  3. customVolatile material was removed by evaporation
  4. customthe residue was triturated with water
  5. washwashed with 10% ammonium hydroxide solution (10 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-2967ab514b094af9a7283e05c5ded4b2
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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