Ammonia → HCID 57389226, compound

HRID 1184734Notes

Reaction equation

HRID 1184734 reaction equation
F[B-](F)(F)F.[N:6]1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([CH:36]2[O:54][C:39]3=[CH:40][N:41]=[C:42]([C:44]4[CH:49]=[CH:48][C:47]([C:50](O)=[O:51])=[CH:46][C:45]=4[F:53])[CH:43]=[C:38]3[CH2:37]2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].C(N(C(C)C)C(C)C)C.N>CN(C)C=O.CO.O>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([CH:36]2[O:54][C:39]3=[CH:40][N:41]=[C:42]([C:44]4[CH:49]=[CH:48][C:47]([C:50](=[O:51])[NH2:6])=[CH:46][C:45]=4[F:53])[CH:43]=[C:38]3[CH2:37]2)[CH2:32][CH2:31]1)=[O:29])([CH3:25])([CH3:26])[CH3:24]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67973511HCID 67973511, compound

Product 1

HCID 57389226HCID 57389226, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (120 mg) is added to a solution of 4-[5-(4-carboxy-2-fluoro-phenyl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (150 mg) and ethyldiisopropylamine (100 mL) in N,N-dimethylformamide (1.50 mL) at room temperature. The mixture is stirred for 10 min prior to the addition of a solution of ammonia in methanol (7 M; 0.50 mL). The resulting mixture stirred at room temperature for 2 h. Water is added and the mixture is extracted with ethyl acetate/methanol. The combined extracts are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate). The crude product is triturated with ethyl acetate, filtered off, washed with diethyl ether and dried to give the title compound. LC (method 7): tR=1.28 min; Mass spectrum (ESI+): m/z=442 [M+H]+.

Workup

  1. stirringThe resulting mixture stirred at room temperature for 2 h
  2. extractionthe mixture is extracted with ethyl acetate/methanol
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel (ethyl acetate)
  7. customThe crude product is triturated with ethyl acetate
  8. filtrationfiltered off
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-834253ccda88493c94bb49d7f54a1581
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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