Methanesulfonamide → HCID 178505180, compound

HRID 2042730Notes

Reaction equation

HRID 2042730 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][C:21]([OH:23])=O)[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH:4]=1.[CH3:26][S:27]([NH2:30])(=[O:29])=[O:28].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:26][S:27]([NH:30][C:21](=[O:23])[CH2:20][C@H:17]1[CH2:18][CH2:19][C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[NH:6][N:7]=[C:3]([C:2]([F:25])([F:24])[F:1])[CH:4]=3)=[CH:9][CH:10]=2)[CH2:15][CH2:16]1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178525542HCID 178525542, compound

Product 1

HCID 178505180HCID 178505180, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 20 mL scintillation vial was added the product from Example 26C (30 mg, 0.085 mmol), methanesulfonamide (9.00 mg, 0.088 mmol), and N,N-dimethylformamide (0.85 mL) followed by O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (39.0 mg, 0.102 mmol) and diisopropylethylamine (30 μL, 0.176 mmol). Following 4 hours of stirring, the solvent was evaporated and the residue purified over RP-HPLC to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.06-1.20 (m, 2 H), 1.43-1.57 (m, 2 H), 1.74-1.91 (m, 5 H), 2.17-2.26 (m, 2 H), 2.41-2.46 (m, 1 H), 6.95-7.22 (m, 1 H), 7.23-7.44 (m, 2 H), 7.64-7.82 (m, 2 H), 11.68 (s, 1 H), 13.98 (s, 1 H); MS (ESI) m/z 430 [M+H]+.

Workup

  1. customthe solvent was evaporated
  2. customthe residue purified over RP-HPLC

Sources & evidence

ORD record
ord-b692a8df1a68447896963f64964d154f
Source dataset
uspto-grants-2013_11
Patent number
US08586594B2

Reaction notes

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