Diisopropylethylamine → HCID 59451929, compound

HRID 1971252Notes

Reaction equation

HRID 1971252 reaction equation
[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([C:24](O)=[O:25])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CCN(C(C)C)C(C)C.[NH:36]1[CH2:40][CH2:39][C@@H:38]([NH:41]C(=O)OC(C)(C)C)[CH2:37]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O.O>[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([C:24]([N:36]5[CH2:40][CH2:39][C@@H:38]([NH2:41])[CH2:37]5)=[O:25])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 59451916HCID 59451916, compound

Product 1

HCID 59451929HCID 59451929, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-{[(1-adamantylmethyl)amino]carbonyl}imidazo[1,2-a]pyridine-2-carboxylic acid (25 mg, 0.071 mmol) in DMF (2 mL) is sequentially added 0.05 mL of DIEA, 15.8 mg of tert-butyl (3R)-pyrrolidin-3-ylcarbamate (0.085 mmol) and 37.6 mg of BOP (0.085 mmol). After stirring for 2 h at RT, the reaction mixture is diluted with EtOAc and water. The organic layer is separated, and the aqueous layer is back extracted with EtOAc. The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. Purification of the residue by PTLC (8% MeOH, 1% NH4OH in DCM) affords the title compound.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is back extracted with EtOAc
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the residue by PTLC (8% MeOH, 1% NH4OH in DCM)

Sources & evidence

ORD record
ord-402be0b14637459688677ba0779069b8
Source dataset
uspto-grants-2013_04
Patent number
US08431593B2

Reaction notes

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