N,N-Dimethylglycine → HCID 69216002, compound

HRID 272683Notes

Reaction equation

HRID 272683 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[C:13]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([O:25][CH3:26])[CH:17]=4)[CH:14]=[CH:15][C:9]=3[C:8](=[O:27])[NH:7][C:6]=2[CH:28]=1.[CH3:29][N:30]([CH2:32][C:33](O)=[O:34])[CH3:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH3:29][N:30]([CH3:31])[CH2:32][C:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[C:13]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([O:25][CH3:26])[CH:17]=4)[CH:14]=[CH:15][C:9]=3[C:8](=[O:27])[NH:7][C:6]=2[CH:28]=1)=[O:34]

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10317380HCID 10317380, compound

Product 1

HCID 69216002HCID 69216002, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 120 (38 mg, 0.10 mmol), dimethylaminoacetic acid (17 mg, 0.12 mmol), HATU (46 mg, 0.12 mmol) and Et3N (0.1 g) in 1 mL of DMF was stirred overnight. The reaction mixture was partitioned between H2O and ethyl acetate, and the organic layer was separated, washed with brine, dried, filtered, and concentrated under vacuum. The residue was purified by preparative HPLC to give the desired product. MS (DCI) m/e 462 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 10.68 (s, 1H), 10.03 (s, 1H), 8.10 (s, 1H), 8.01 (d, J=8.59 Hz, 1H), 7.80 (d, J=8.29 Hz, 1H), 7.53 (d, J=1.23 Hz, 1H), 7.43 (s, 1H), 7.21-7.36 (m, 4H), 7.03 (d, J=8.59 Hz, 1H), 4.11 (s, 2H), 4.03 (s, 3H), 2.86 (s, 6H).

Workup

  1. customThe reaction mixture was partitioned between H2O and ethyl acetate
  2. customthe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f958b360024a4cbe97a11df7d1ff0391
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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