2-Pyridineethanamine → HCID 86670467, compound

HRID 1911850Notes

Reaction equation

HRID 1911850 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[C:10]([O:14][C:15]([N:17]1[C@@H:21]([C@H:22]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:19][C@H:18]1[CH2:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](O)=[O:43])=[CH:40][CH:39]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Si:30]([O:29][C@H:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C@H:21]1[CH2:20][CH2:19][C@@H:18]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([C:42](=[O:43])[NH:1][CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=3)=[CH:45][CH:46]=2)[N:17]1[C:15]([O:14][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:16])([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 759192-PyridineethanamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67971935HCID 67971935, compound

Product 1

HCID 86670467HCID 86670467, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(2-Aminoethyl)pyridine (0.034 mL, 0.29 mmol) was added to a stirred, room temperature mixture of 4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)benzoic acid (100 mg, 0.190 mmol), HATU (87 mg, 0.228 mmol), and DIPEA (0.166 mL, 0.951 mmol) in DMF (1.9 ml). The resulting mixture was stirred at room temperature overnight. Upon completion, as determined by LC-MS, water was added, and the mixture was partitioned with EtOAc. The aqueous layer was extracted with EtOAc (3×), and the combined organic layers were washed with brine, dried with Na2SO4, filtered, and concentrated in vacuo to give the product that was used directly in the next step. LC-MS=630.3 (M+1)+.

Workup

  1. additionwas added
  2. customthe mixture was partitioned with EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the product that

Sources & evidence

ORD record
ord-700f5e266e644f879d8d4dd7327ded6c
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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