Acetylglycine → HCID 67380402, compound

HRID 1850657Notes

Reaction equation

HRID 1850657 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:42]1([N:47]2[C:51]3[N:52]=[C:53]([NH:56][C:57]4[CH:62]=[CH:61][C:60]([N:63]5[C:70](=[O:71])[CH2:69][C@@H:68]6[NH:72][C@@H:65]([CH2:66][CH2:67]6)[CH2:64]5)=[CH:59][N:58]=4)[N:54]=[CH:55][C:50]=3[CH:49]=[C:48]2[C:73]([N:75]([CH3:77])[CH3:76])=[O:74])[CH2:46][CH2:45][CH2:44][CH2:43]1>CN(C=O)C.[Cl-].[Na+].O>[C:1]([NH:4][CH2:5][C:6]([N:72]1[C@@H:68]2[CH2:67][CH2:66][C@H:65]1[CH2:64][N:63]([C:60]1[CH:61]=[CH:62][C:57]([NH:56][C:53]3[N:54]=[CH:55][C:50]4[CH:49]=[C:48]([C:73]([N:75]([CH3:77])[CH3:76])=[O:74])[N:47]([CH:42]5[CH2:46][CH2:45][CH2:44][CH2:43]5)[C:51]=4[N:52]=3)=[N:58][CH:59]=1)[C:70](=[O:71])[CH2:69]2)=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 10972AcetylglycineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53377611HCID 53377611, compound

Product 1

HCID 67380402HCID 67380402, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Acetamidoacetic acid (12 mg, 0.102 mmol) was combined with diisopropylethylamine (0.018 ml, 0.102 mmol) and HBTU (38.8 mg, 0.102 mmol) in DMF (1 ml) for 15 min. 7-Cyclopentyl-N,N-dimethyl-2-(5-((1S,6R)-4-oxo-3,9-diazabicyclo[4.2.1]nonan-3-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (50 mg, 0.102 mmol) was then added and the reaction allowed to stir for 4 hrs. The reaction was then poured into brine and extracted with ethyl acetate. The combined ethyl acetate extracts were dried with sodium sulfate, filtered, concentrated and the resulting residue purified by silica gel chromatography which gave 2-(5-((1S,6R)-9-(2-acetamidoacetyl)-4-oxo-3,9-diazabicyclo[4.2.1]nonan-3-yl)pyridin-2-ylamino)-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (45 mg) in 77% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.71 (d, J=8.08 Hz, 2H), 8.82 (s, 1H), 8.14 (d, J=2.53 Hz, 1H), 8.07 (d, J=6.06 Hz, 1H), 7.61 (d, J=9.09 Hz, 2H), 6.63 (s, 2H), 4.76 (m, 2H), 4.53 (br. s., 1H), 4.44 (br. s., 0H), 4.21 (d, J=14.65 Hz, 0H), 3.95 (m, 2H), 3.61 (dd, J=14.91, 5.81 Hz, 1H), 3.04 (m, 6H), 2.78 (m, 1H), 2.40 (m, 3H), 2.00 (m, 6H), 1.89 (s, 3H), 1.66 (m, 3H). MS ink 588.6 (M+H)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined ethyl acetate extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe resulting residue purified by silica gel chromatography which

Sources & evidence

ORD record
ord-2dff00ceb32047558a28f9cfccad94b8
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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